Organic semiconductor element, manufacturing method thereof, composition for forming organic semiconductor film, compound, and organic semiconductor film

ABSTRACT

An object to be achieved by the present invention is to provide an organic semiconductor element and an organic semiconductor film having high mobility and excellent heat resistance, and a manufacturing method thereof, to provide a novel compound that is suitable as an organic semiconductor, and to provide a composition for forming an organic semiconductor film in which coating film formability is excellent, with which an organic semiconductor element that has high mobility can be obtained, and in which heat resistance is excellent, an organic semiconductor element in which the composition for forming an organic semiconductor film is used, and a manufacturing method thereof. 
     The organic semiconductor element according to the present invention includes a compound represented by Formula 1 below included in an organic semiconductor layer.

CROSS-REFERENCE TO RELATED APPLICATION

This application is a continuation application of InternationalApplication No. PCT/JP2015/082668, filed Nov. 20, 2015, the disclosureof which is incorporated herein by reference in its entirety. Further,this application claims priority from Japanese Patent Application No.2014-237888, filed Nov. 25, 2014, the disclosure of which isincorporated herein by reference in its entirety.

BACKGROUND OF THE INVENTION

1. Field of the Invention

The present invention relates to an organic semiconductor element, amanufacturing method thereof, a composition for forming an organicsemiconductor film, a compound, and an organic semiconductor film.

2. Description of the Related Art

An organic transistor having an organic semiconductor film (organicsemiconductor layer) is used in a field effect transistor (FET) used ina liquid crystal display or an organic electroluminescence (EL) display,Radio Frequency Identifier (RFID, RF tag), and the like, becauselightening of weight, cost reduction and flexibilization can beachieved.

As the organic semiconductor in the related art, those disclosed inJP2010-177637A and WO2013/168048A are known.

SUMMARY OF THE INVENTION

An object to be achieved by the present invention is to provide anorganic semiconductor element and an organic semiconductor film havinghigh mobility and excellent heat resistance, and a manufacturing methodthereof.

Another object to be achieved by the present invention is to provide anovel compound that is suitable as an organic semiconductor.

Still another object to be achieved by the present invention is toprovide a composition for forming an organic semiconductor film in whichcoating film formability is excellent, with which an organicsemiconductor element that has high mobility can be obtained, and inwhich heat resistance is excellent, an organic semiconductor element inwhich the composition for forming an organic semiconductor film is used,and a manufacturing method thereof.

The objects of the present invention are solved by the means describedin <1>, <17>, <34>, <35>, <37>, <38>, and <40> below. <1> to <16>, <18>to <33>, <36>, and <39> which are preferable embodiments are alsodescribed below.

<1> An organic semiconductor element comprising: a compound representedby Formula 1 below in an organic semiconductor layer,

in Formula 1, X¹¹ and X¹² each independently represent a chalcogen atom,Z^(1a) to Z^(1j) each independently represent a hydrogen atom or ahalogen atom, A¹¹ represents ═CR^(A11)— or a nitrogen atom, R^(A11)represents a hydrogen atom or a group represented by R¹¹, A¹² represents═CR^(A12)— or a nitrogen atom, R^(A12) represents a hydrogen atom or agroup represented by R¹², n1 represents 0 or 1, p1 represents an integerof 0 to 2 in a case where A¹¹ is ═CR^(A11)— and represents 0 or 1 in acase where A¹¹ is a nitrogen atom, q1 represents an integer of 0 to 2 ina case where A¹² is ═CR^(A12)— and represents 0 or 1 in a case where A¹²is a nitrogen atom, R¹¹ and R¹² each independently represent a halogenatom, an aryl group, a heteroaryl group, or a group represented byFormula W below, and—S^(W)-L^(W)-T^(W)  (W)

in Formula W, S^(W) represents a single bond or an alkylene grouprepresented by —(CR^(S) ₂)_(k)—, R^(S) each independently represent ahydrogen atom or a halogen atom, k represents an integer of 1 to 17,L^(W) represents a single bond, a divalent linking group represented byany one of Formulae L-1 to L-16 below, or a group obtained by bondingany two or more of divalent linking groups represented by Formulae L-1to L-16 below, T^(W) represents an alkyl group, a cyano group, a vinylgroup, an ethynyl group, an aryl group, a heteroaryl group, anoxyethylene group, an oligooxyethylene group of which the repetitionnumber of oxyethylene units is two or greater, an oligosiloxane grouphaving two or more silicon atoms, or a trialkylsilyl group,

in Formulae L-1 to L-16, * and wavy line portions represent bondingpositions to other structures, p13 represents an integer of 0 to 4, p14,p15, and p16 each independently represent an integer of 0 to 2, R^(L1),R^(L21), R^(L22), R^(L13), R^(L14), R^(L15), and R^(L16) eachindependently represent a hydrogen atom or a substituent.

<2> The organic semiconductor element according to <1>, in which all ofZ^(1a) to Z^(1j) are hydrogen atoms.

<3> The organic semiconductor element according to <1> or <2>, in whichn1 is 0.

<4> The organic semiconductor element according to any one of <1> to<3>, in which at least one of p1 or q1 is not 0.

<5> The organic semiconductor element according to any one of <1> to<4>, in which at least one of p1 or q1 is not 0, and at least one of R¹¹or R¹² is a group represented by Formula W.

<6> The organic semiconductor element according to any one of <1> to<5>, in which p1 and q1 are 1.

<7> The organic semiconductor element according to any one of <1> to<6>, in which both of X¹¹ and X¹² are S atoms, A¹¹ is ═CR^(A11)—, andA¹² is ═CR^(A12)—.

<8> The organic semiconductor element according to any one of <1> to<6>, in which a compound represented by Formula 1 is a compoundrepresented by Formula 2 below,

in Formula 2, X²¹ and X²² each independently represent a chalcogen atom,W²¹ and W²² each independently represent a group represented by FormulaW.

<9> The organic semiconductor element according to any one of <1> to<8>, in which the compound represented by Formula 1 is a line symmetricstructure.

<10> The organic semiconductor element according to any one of <1> to<9>, in which the number of carbon atoms in the group represented byFormula W is 5 to 40.

<11> The organic semiconductor element according to any one of <1> to<10>, in which L^(W) is a single bond, a divalent linking grouprepresented by any one of Formulae L-1 to L-4 and Formulae L-13 to L-16,or a divalent linking group obtained by bonding two or more divalentlinking groups represented by any one of Formulae L-1 to L-4 andFormulae L-13 to L-16.

<12> The organic semiconductor element according to any one of <1> to<11>, in which L^(W) is a single bond or a divalent linking grouprepresented by any one of Formulae L-1 to L-4 and Formulae L-13 to L-16.

<13> The organic semiconductor element according to any one of <1> to<12>, in which S^(W) is a single bond.

<14> The organic semiconductor element according to any one of <1> to<13>, in which L^(W) is a single bond or a divalent linking grouprepresented by any one of Formula L-1 and Formulae L-13 to L-16.

<15> The organic semiconductor element according to any one of <1> to<14>, in which T^(W) is an alkyl group.

<16> The organic semiconductor element according to any one of <1> to<15>, in which a group represented by Formula W is an alkyl group.

<17> A composition for forming an organic semiconductor film,comprising: a solvent having a boiling point of 100° C. or higher; and acompound represented by Formula 1, in which a content of the compoundrepresented by Formula 1 is 20 mass % or less with respect to a totalamount of the composition for forming an organic semiconductor film.

<18> The composition for forming an organic semiconductor film accordingto <17>, in which all of Z^(1a) to Z^(1j) are hydrogen atoms.

<19> The composition for forming an organic semiconductor film accordingto <17> or <18>, in which n1 is 0.

<20> The composition for forming an organic semiconductor film accordingto any one of <17> to <19>, in which at least one of p1 or q1 is not 0.

<21> The composition for forming an organic semiconductor film accordingto any one of <17> to <20>, in which at least one of p1 or q1 is not 0,and at least one of R¹¹ or R¹² is a group represented by Formula W.

<22> The composition for forming an organic semiconductor film accordingto any one of <17> to <21>, in which p1 and q1 is 1.

<23> The composition for forming an organic semiconductor film accordingto any one of <17> to <22>, in which both of X¹¹ and X¹² are S atoms,A¹¹ is ═CR^(A11)—, and A¹² is ═CR^(A12)—.

<24> The composition for forming an organic semiconductor film accordingto any one of <17> to <22>, in which the compound represented by Formula1 is a compound represented by Formula 2.

<25> The composition for forming an organic semiconductor film accordingto any one of <17> to <24>, in which the compound represented by Formula1 is a line symmetric structure.

<26> The composition for forming an organic semiconductor film accordingto any one of <17> to <25>, in which the number of carbon atoms in thegroup represented by Formula W is 5 to 40.

<27> The composition for forming an organic semiconductor film accordingto any one of <17> to <26>, in which L^(W) is a single bond, a divalentlinking group represented by any one of Formulae L-1 to L-4 and FormulaeL-13 to L-16, and a divalent linking group obtained by bonding two ormore divalent linking groups represented by any one of Formulae L-1 toL-4 and Formulae L-13 to L-16.

<28> The composition for forming an organic semiconductor film accordingto any one of <17> to <27>, in which L^(W) is a single bond or adivalent linking group represented by any one of Formulae L-1 to L-4 andFormulae L-13 to L-16.

<29> The composition for forming an organic semiconductor film accordingto any one of <17> to <28>, in which S^(W) is a single bond.

<30> The composition for forming an organic semiconductor film accordingto any one of <17> to <29>, in which L^(W) is a single bond or adivalent linking group represented by any one of Formula L-1 andFormulae L-13 to L-16.

<31> The composition for forming an organic semiconductor film accordingto any one of <17> to <30>, in which T^(W) is an alkyl group.

<32> The composition for forming an organic semiconductor film accordingto any one of <17> to <31>, in which a group represented by Formula W isan alkyl group.

<33> The composition for forming an organic semiconductor film accordingto any one of <17> to <32>, further comprising: a binder polymer, inwhich a content of the binder polymer is 10 mass % or less with respectto a total amount of the composition for forming an organicsemiconductor film.

<34> A compound represented by Formula 1.

<35> A method of manufacturing an organic semiconductor film,comprising: an applying step of applying the composition for forming anorganic semiconductor film according to any one of <17> to <33> to asubstrate, and a removing step of removing at least a portion of thesolvent having a boiling point of 100° C. or higher included in thecomposition for forming an organic semiconductor film.

<36> The method of manufacturing the organic semiconductor filmaccording to <35>, in which the applying step is performed by an ink jetmethod or a flexographic printing method.

<37> An organic semiconductor film obtained by the method according to<35> or <36>.

<38> A method of manufacturing an organic semiconductor element,comprising: an applying step of applying the composition for forming anorganic semiconductor film according to any one of <17> to <33> to asubstrate, and a removing step of removing at least a portion of thesolvent having a boiling point of 100° C. or higher included in thecomposition for forming an organic semiconductor film.

<39> The method of manufacturing the organic semiconductor elementaccording to <38>, in which the applying step is performed by an ink jetmethod or a flexographic printing method.

<40> An organic semiconductor element manufactured by the methodaccording to <38> or <39>.

According to the present invention, it is possible to provide an organicsemiconductor element and an organic semiconductor film having highmobility and excellent heat resistance, and a manufacturing methodthereof.

According to the present invention, it is possible to provide a novelcompound that is suitable as an organic semiconductor.

According to the present invention, it is possible to provide acomposition for forming an organic semiconductor film in which coatingfilm formability is excellent, with which an organic semiconductorelement that has high mobility can be obtained, and in which heatresistance is excellent, an organic semiconductor element in which thecomposition for forming an organic semiconductor film is used, and amanufacturing method thereof.

BRIEF DESCRIPTION OF THE DRAWINGS

FIG. 1 is a schematic cross-sectional view of an aspect of an organicsemiconductor element of the present invention.

FIG. 2 is a schematic cross-sectional view of another aspect of theorganic semiconductor element of the present invention.

DESCRIPTION OF THE PREFERRED EMBODIMENTS

Hereinafter, the contents of the present invention will be specificallydescribed. The constituents in the following description will beexplained based on typical embodiments of the present invention, but thepresent invention is not limited to the embodiments. In thespecification of the present application, “to” is used to mean that thenumerical values listed before and after “to” are a lower limit and anupper limit respectively. Furthermore, in the present invention, anorganic EL element refers to an organic electroluminescence element.

In the present specification, in a case where there is no descriptionregarding whether a group (atomic group) is substituted orunsubstituted, the group includes both of a group having a substituentand a group not having a substituent. For example, an “alkyl group”includes not only an alkyl group not having a substituent (unsubstitutedalkyl group) but also an alkyl group having a substituent (substitutedalkyl group).

In the present specification, in some cases, a chemical structuralformula is described as a simplified structural formula in which ahydrogen atom is omitted.

In the present invention, “mass %” and “weight %” have the samedefinition, and “part by mass” and “part by weight” have the samedefinition.

In the present invention, a combination of preferred aspects is morepreferable.

(Organic Semiconductor Element and Compound)

The organic semiconductor element according to the present inventionincludes a compound (hereinafter, referred to as a “specific compound”)represented by Formula 1 above in an organic semiconductor layer.

The compound represented by Formula 1 above is preferably an organicsemiconductor compound.

As a result of diligent research, the present inventors found that anorganic semiconductor element or an organic semiconductor filmcontaining the compound represented by Formula 1 has high mobility andexcellent heat resistance, so as to complete the present invention.

A specific mechanism for exhibiting the effect is not clear, but it isassumed that if the compound represented by Formula 1 has line symmetrywith a molecular center as an axis of symmetry in a certain degree orgreater, mobility improves since crystallinity becomes excellent, andheat resistance of the organic semiconductor element is improved since amelting point increases.

It is assumed that crystallinity is excellent and mobility is improved,since the compound represented by Formula 1 has a molecular shape thatthe terminal thiophene ring protrudes from a rod-like structure such asa phenanthrene structure or a picene structure, and the appearance of aliquid crystal layer is suppressed. The mechanism of the suppression ofthe appearance of the liquid crystal layer as above contributes to theimprovement of the heat resistance of the organic semiconductor element.

<Specific Compound>

The specific compound according to the present invention is representedby Formula 1 below.

In Formula 1, X¹¹ and X¹² each independently represent a chalcogen atom,Z^(1a) to Z^(1j) each independently represent a hydrogen atom or ahalogen atom, A¹¹ represents ═CR^(A11)— or a nitrogen atom, R^(A11)represents a hydrogen atom or a group represented by R¹¹, A¹² represents═CR^(A12)— or a nitrogen atom, R^(A12) represents a hydrogen atom or agroup represented by R¹², n1 represents 0 or 1, p1 represents an integerof 0 to 2 in a case where A¹¹ is ═CR^(A11)— and represents 0 or 1 in acase where A¹¹ is a nitrogen atom, q1 represents an integer of 0 to 2 ina case where A¹² is ═CR^(A12)— and represents 0 or 1 in a case where A¹²is a nitrogen atom, R¹¹ and R¹² each independently represent a halogenatom, an aryl group, a heteroaryl group, or a group represented byFormula W below.—S^(W)-L^(W)-T^(W)  (W)

In Formula W, S^(W) represents a single bond or an alkylene grouprepresented by —(CR^(S) ₂)_(k)—, R^(S) each independently represent ahydrogen atom or a halogen atom, k represents an integer of 1 to 17,L^(W) represents a single bond, a divalent linking group represented byany one of Formulae L-1 to L-16 below, or a group obtained by bondingany two or more of divalent linking groups represented by Formulae L-1to L-16 below, T^(W) represents an alkyl group, a cyano group, a vinylgroup, an ethynyl group, an aryl group, a heteroaryl group, anoxycthylene group, an oligooxycthylene group of which the repetitionnumber of oxyethylene units is two or greater, an oligosiloxane grouphaving two or more silicon atoms, or a trialkylsilyl group.

In Formulae L-1 to L-16, * and wavy line portions represent bondingpositions to other structures, p13 represents an integer of 0 to 4, p14,p15, and p16 each independently represent an integer of 0 to 2, R^(L1),R^(L21), R^(L22), R^(L13), R^(L14), R^(L15), and R^(L16) eachindependently represent a hydrogen atom or a substituent.

The specific compound according to the present invention is preferablyan organic semiconductor compound.

The specific compound according to the present invention is a novelcompound.

The specific compound according to the present invention can be suitablyused for an organic semiconductor element, an organic semiconductorfilm, and a composition for forming an organic semiconductor film.

In Formula 1, X¹¹ and X¹² each independently represent a chalcogen atom,it is preferable that X¹¹ and X¹² each independently represent an O atomor an S atom, and it is more preferable that both of X¹¹ and X¹² are Satoms. The chalcogen atom refers to an atom in Group 16 including an Oatom.

Z^(1a) to Z^(1j) each independently represent a hydrogen atom or ahalogen atom, and it is preferable that all of Z^(1a) to Z^(1j) arehydrogen atoms.

Examples of the halogen atom include a fluorine atom, a chlorine atom, abromine atom, and an iodine atom, and a fluorine atom is preferable.

A¹¹ represents ═CR^(A11)— or an nitrogen atom, and ═CR^(A11)— ispreferable.

R^(A11) represents a hydrogen atom or a group represented by R¹¹, and ahydrogen atom is preferable. The expression “R^(A11) represents a grouprepresented by R¹¹” refers to a case where one of R¹¹'s of which thenumber is specified by p1 in Formula 1 is bonded to a carbon atom inA¹¹.

A¹² represents ═CR^(A12)— or a nitrogen atom, and ═CR^(A12)— ispreferable.

R^(A12) represents a hydrogen atom or a group represented by R¹², and ahydrogen atom is preferable. The expression “R^(A12) represents a grouprepresented by R¹²” refers to a case where one of R¹²'s of which thenumber is specified by q1 in Formula 1 is bonded to a carbon atom in A².

n1 represents 0 or 1 and preferably 0.

In a case where A¹¹ is ═CR^(A11)—, p1 represents an integer of 0 to 2,preferably represents 1 or 2, more preferably 1. In a case where A¹¹ isa nitrogen atom, p1 represents 0 or 1 and preferably represents 1. In acase where A¹¹ is ═CR^(A11)—, and p1 is 1, R¹¹ is preferably bonded to acarbon atom positioned between A¹¹ and X¹¹, not a carbon atom includedin A¹¹.

In a case where A¹² is ═CR^(A12)—, q1 represents an integer of 0 to 2,preferably represents 1 or 2, and more preferably represents 1. In acase where A¹² is a nitrogen atom, q1 represents 0 or 1 and preferablyrepresents 1. In a case where A¹² is ═CR^(A12)— and q1 is 1, R¹² ispreferably bonded to a carbon atom positioned between A¹² and X¹², not acarbon atom included in A¹².

R¹¹ and R¹² each independently represent a halogen atom, an aryl group,a heteroaryl group, or a group represented by Formula W below andpreferably represents a group represented by Formula W.—S^(W)-L^(W)-T^(W)  (W)

In Formula W, S^(W) represents a single bond or an alkylene grouprepresented by —(CR^(S) ₂)_(k)— and preferably represents a single bond.

R^(S) each independently represent a hydrogen atom or a halogen atom andpreferably a hydrogen atom.

k represents an integer of 1 to 17, preferably represents an integer of1 to 15, and more preferably an integer of 1 to 10.

L^(W) represents a single bond, a divalent linking group represented byany one of Formulae L-1 to L-16, or a group obtained by bonding any twoor more of divalent linking groups represented by Formulae L-1 to L-16,preferably represents a single bond, a divalent linking grouprepresented by any one of Formulae L-1 to L-4 and Formulae L-13 to L-16,or a divalent linking group obtained by bonding two or more divalentlinking groups represented by any one of Formulae L-1 to L-4 andFormulae L-13 to L-16, more preferably a single bond or a divalentlinking group represented by any one of Formulae L-1 to L-4 and FormulaeL-13 to L-16, and even more preferably a divalent linking grouprepresented by any one of Formulae L-1, L-3, L-15, and L-16.

L^(W) preferably represents a single bond or a divalent linking grouprepresented by any one of Formula L-1 and Formulae L-13 to L-16.

T^(W) represented by an alkyl group, a cyano group, a vinyl group, anethynyl group, an aryl group, a heteroaryl group, an oxyethylene group,an oligooxyethylene group of which the repetition number of oxyethyleneunits is two or greater, an oligosiloxane group having two or moresilicon atoms, or a trialkylsilyl group.

The alkyl group is preferably an alkyl group having 2 to 18 carbonatoms, more preferably an alkyl group having 3 to 15 carbon atoms, andeven more preferably an alkyl group having 4 to 13 carbon atoms. Thealkyl group may have any one of a linear shape, a branched shape, or acyclic shape, or may have a structure obtained by combining these.However, a linear or branched alkyl group is preferable, and a linearalkyl group is more preferable.

The alkyl group may be substituted and preferable examples of thesubstituent include a halogen atom.

Examples of the aryl group (an aromatic hydrocarbon group) include agroup obtained by removing one hydrogen atom from benzene, naphthalene,anthracene, or the like. A group obtained by removing one hydrogen atomfrom benzene is preferable.

The aryl group may be substituted but is preferably not substituted.

Examples of a heteroatom included in a heteroaryl group (an aromaticheterocyclic group) include an oxygen atom, a nitrogen atom, and asulfur atom. An oxygen atom and a sulfur atom are preferable, and asulfur atom is more preferable.

Examples of the heteroaryl group include a group obtained by removingone hydrogen atom from a thiophene ring, a furan ring, a pyran ring, apyrrole ring, a pyridine ring, a pyrazine ring, a pyrimidine ring, apyridazine ring, a selenophene ring, an imidazole ring, and the like. Agroup obtained by removing one hydrogen atom from a thiophene ring or afuran ring is more preferable, and a group obtained by removing onehydrogen atom from a thiophene ring is even more preferable.

The heteroaryl group may be further substituted, but it is preferablethat the heteroaryl group is not substituted.

The oligooxyethylene group of which the repetition number of oxyethyleneunits is two or greater is preferably an oligooxyethylene group of whichthe repetition number is one to five and more preferably anoligooxyethylene group of which the repetition number is one to three.

The oligosiloxane group having two or more silicon atoms is preferablyan oligosiloxane group having one to five silicon atoms and morepreferably an oligosiloxane group having one to three silicon atoms.

In Formulae L-1 to L-16, it is preferable that wavy line portionsrepresent bonding positions to S^(W), * represents a bonding position toT^(W) or a bonding position to a divalent linking group selected fromthe group consisting of other L-1 to L-16.

p13 represents an integer of 0 to 4, p14, p15, and p16 eachindependently represent an integer of 0 to 2, and R^(L1), R^(L21),R^(L22), R^(L13), R^(L14), R^(L15), and R^(L16) each independentlyrepresent a hydrogen atom or a substituent.

In a case where L^(W) represents a linking group obtained by bonding adivalent linking group represented by any one of Formulae L-1 to L-16above, the number of linkages of the divalent linking groups representedby any one of Formulae L-1 to L-16 is preferably 2 to 4 and morepreferably 2 or 3.

R^(L1), R^(L21), R^(L22), R^(L13), R^(L14), R^(L15), and R^(L16) eachindependently represent a hydrogen atom or a substituent and preferablyrepresent a hydrogen atom. Examples of the substituent include varioussubstituents exemplified as T^(W) in Formula 1 above.

A plurality of R^(L1)'s, R^(L13)'s, R^(L14)'s, R^(L15)'s, and R^(L16)'smay be identical to or different from each other. R^(L1)'s, R^(L21)'s,and R^(L22)'s may form ring structures by being bonded to T^(W) adjacentto each other or may form a fused ring as the ring structure.

The group represented by Formula W is preferably an alkyl group, morepreferably an alkyl group having 2 to 18 carbon atoms, even morepreferably an alkyl group having 3 to 15 carbon atoms, and particularlypreferably an alkyl group having 4 to 13 carbon atoms. In a case wherethe group represented by Formula W is an alkyl group, it is preferablethat S^(W) and L^(W) are single bonds, and T^(W) is an alkyl group.

In Formula 1, it is preferable that at least one of p1 or q1 is not 0,and it is more preferable that at least one of p1 or q1 is not 0, and atleast one of R¹¹ or R¹² is a group represented by Formula W.

In Formula 1, it is preferable that p1 and q1 are 1, it is morepreferable that p1 and q1 are 1, and at least one of R¹¹ or R¹² is agroup represented by Formula W, and it is even more preferable that p1and q1 are 1, and both of R¹¹ and R¹² are groups represented by FormulaW.

In Formula 1, it is preferable that both of X¹¹ and X¹² are S atoms, A¹¹is ═CR^(A11)—, and A¹² is ═CR^(A12)—, it is more preferable that both ofX¹¹ and X¹² are S atoms, A¹¹ is ═CR^(A11)—, A¹² is ═CR^(A12)—, and bothof R^(A11) and R^(A12) are hydrogen atoms.

The compound represented by Formula 1 is preferably a compoundrepresented by Formula 2 below.

In Formula 2, X²¹ and X²² each independently represent a chalcogen atom,preferably an O atom or a S atom. It is more preferable that both of X²¹and X²² are S atoms. W²¹ and W²² each independently represent a grouprepresented by Formula W above, and a preferable aspect thereof is thesame as the preferable aspect described in the group represented byFormula W above.

The compound represented by Formula 1 above is preferably a linesymmetric structure.

The expression “a compound has a line symmetric structure” means that astructural formula thereof is line symmetric with respect to the entiremolecule. Specifically, the compound represented by Formula 1 ispreferably a compound represented by Formulae 3 to 5 below.

It is considered that, if the compound represented by Formula 1 has aline symmetric structure, crystallinity and melting point become high,and mobility or heat resistance of an obtained organic semiconductorelement or an obtained organic semiconductor film increase.

In Formula 3 or 4, X¹¹, X¹², Z^(1a) to Z^(1j), A¹¹, A¹², p1, q1, R¹¹,and R¹² have the same meaning as X¹¹, X¹², Z^(1a) to Z^(1j), A¹¹, A¹²,p1, q1, R¹¹, and R¹² in Formula 1, and preferable aspects thereof arealso the same.

In Formula 5, X²¹, X²², W²¹, and W²² have the same meaning as X²¹, X²²,W²¹, and W²² in Formula 2, and preferable aspects thereof are also thesame.

All of the compounds represented by Formulae 3 to 5 have line symmetryhaving broken lines as symmetry axes.

As specific examples of the specific compound used in the presentinvention, Compounds 1 to 1475 represented by Formulae a to c below andpresented in Tables 1 to 59 are preferably exemplified. However, thepresent invention is not limited thereto.

In Compounds 1 to 1475, X^(a1), X^(a2), R^(a11), R^(a12), R^(a21),R^(a22), X^(b1), X^(b2), R^(b11), R^(b12), R^(b21), R^(b22), X^(c1),X^(c2), R^(c11), and R^(c21) in Formulae a to c represent structurespresented in Tables 1 to 59. In Tables 1 to 59, Ph represents a phenylgroup, -Ph- represents a phenylene group, and * represents a bondingportion to another structure.

TABLE 1 X^(a1) X^(a2) R^(a11) R^(a12) R^(a21) R^(a22) Compound 1 S SC₄H₉—* H C₄H₉—* H Compound 2 S S C₅H₁₁—* H C₅H₁₁—* H Compound 3 S SC₆H₁₃—* H C₆H₁₃—* H Compound 4 S S C₇H₁₅—* H C₇H₁₅—* H Compound 5 S SC₈H₁₇—* H C₈H₁₇—* H Compound 6 S S C₉H₁₉—* H C₉H₁₉—* H Compound 7 S SC₁₀H₂₁—* H C₁₀H₂₁—* H Compound 8 S S C₁₁H₂₃—* H C₁₁H₂₃—* H Compound 9 SS C₁₂H₂₅—* H C₁₂H₂₅—* H Compound 10 S S C₁₃H₂₇—* H C₁₃H₂₇—* H Compound11 S S C₁₄H₂₉—* H C₁₄H₂₉—* H Compound 12 S S C₁₅H₃₁—* H C₁₅H₃₁—* HCompound 13 S S C₁₆H₃₃—* H C₁₆H₃₃—* H Compound 14 S S C₁₇H₃₅—* HC₁₇H₃₅—* H Compound 15 S S C₁₈H₃₇—* H C₁₈H₃₇—* H Compound 16 S S C₅H₁₁—*C₅H₁₁—* C₅H₁₁—* C₅H₁₁—* Compound 17 S S C₆H₁₃—* C₆H₁₃—* C₆H₁₃—* C₆H₁₃—*Compound 18 S S C₇H₁₅—* C₇H₁₅—* C₇H₁₅—* C₇H₁₅—* Compound 19 S S C₈H₁₇—*C₈H₁₇—* C₈H₁₇—* C₈H₁₇—* Compound 20 S S C₉H₁₉—* C₉H₁₉—* C₉H₁₉—* C₉H₁₉—*Compound 21 S S C₁₀H₂₁—* C₁₀H₂₁—* C₁₀H₂₁—* C₁₀H₂₁—* Compound 22 S SC₁₁H₂₃—* C₁₁H₂₃—* C₁₁H₂₃—* C₁₁H₂₃—* Compound 23 S S C₁₂H₂₅—* C₁₂H₂₅—*C₁₂H₂₅—* C₁₂H₂₅—* Compound 24 S S C₁₃H₂₇—* C₁₃H₂₇—* C₁₃H₂₇—* C₁₃H₂₇—*Compound 25 S S C₁₄H₂₉—* C₁₄H₂₉—* C₁₄H₂₉—* C₁₄H₂₉—* Compound 26 S SC₁₅H₃₁—* C₁₅H₃₁—* C₁₅H₃₁—* C₁₅H₃₁—* Compound 27 S S C₁₆H₃₃—* C₁₆H₃₃—*C₁₆H₃₃—* C₁₆H₃₃—* Compound 28 S S C₁₇H₃₅—* C₁₇H₃₅—* C₁₇H₃₅—* C₁₇H₃₅—*Compound 29 S S C₁₈H₃₇—* C₁₈H₃₇—* C₁₈H₃₇—* C₁₈H₃₇—* Compound 30 S Sp-C₅H₁₁—Ph—* H p-C₅H₁₁—Ph—* H Compound 31 S S p-C₆H₁₃—Ph—* Hp-C₆H₁₃—Ph—* H Compound 32 S S p-C₇H₁₅—Ph—* H p-C₇H₁₅—Ph—* H Compound 33S S p-C₈H₁₇—Ph—* H p-C₈H₁₇—Ph—* H Compound 34 S S p-C₉H₁₉—Ph—* Hp-C₉H₁₉—Ph—* H Compound 35 S S p-C₁₀H₂₁—Ph—* H p-C₁₀H₂₁—Ph—* H Compound36 S S p-C₁₁H₂₃—Ph—* H p-C₁₁H₂₃—Ph—* H Compound 37 S S p-C₁₂H₂₅—Ph—* Hp-C₁₂H₂₅—Ph—* H Compound 38 S S p-C₁₃H₂₇—Ph—* H p-C₁₃H₂₇—Ph—* H Compound39 S S p-C₁₄H₂₉—Ph—* H p-C₁₄H₂₉—Ph—* H Compound 40 S S p-C₁₅H₃₁—Ph—* Hp-C₁₅H₃₁—Ph—* H Compound 41 S S p-C₁₆H₃₃—Ph—* H p-C₁₆H₃₃—Ph—* H Compound42 S S p-C₁₇H₃₅—Ph—* H p-C₁₇H₃₅—Ph—* H Compound 43 S S p-C₁₈H₃₇—Ph—* Hp-C₁₈H₃₇—Ph—* H Compound 44 S S p-C₅H₁₁—Ph—* p-C₅H₁₁—Ph—* p-C₅H₁₁—Ph—*p-C₅H₁₁—Ph—* Compound 45 S S p-C₆H₁₃—Ph—* p-C₆H₁₃—Ph—* p-C₆H₁₃—Ph—*p-C₆H₁₃—Ph—* Compound 46 S S p-C₇H₁₅—Ph—* p-C₇H₁₅—Ph—* p-C₇H₁₅—Ph—*p-C₇H₁₅—Ph—* Compound 47 S S p-C₈H₁₇—Ph—* p-C₈H₁₇—Ph—* p-C₈H₁₇—Ph—*p-C₈H₁₇—Ph—* Compound 48 S S p-C₉H₁₉—Ph—* p-C₉H₁₉—Ph—* p-C₉H₁₉—Ph—*p-C₉H₁₉—Ph—* Compound 49 S S p-C₁₀H₂₁—Ph—* p-C₁₀H₂₁—Ph—* p-C₁₀H₂₁—Ph—*p-C₁₀H₂₁—Ph—* Compound 50 S S p-C₁₁H₂₃—Ph—* p-C₁₁H₂₃—Ph—* p-C₁₁H₂₃—Ph—*p-C₁₁H₂₃—Ph—* Compound 51 S S p-C₁₂H₂₅—Ph—* p-C₁₂H₂₅—Ph—* p-C₁₂H₂₅—Ph—*p-C₁₂H₂₅—Ph—*

TABLE 2 X^(a1) X^(a2) R^(a11) R^(a12) R^(a21) R^(a22) Compound 52 S Sp-C₁₃H₂₇—Ph—* p-C₁₃H₂₇—Ph—* p-C₁₃H₂₇—Ph—* p-C₁₃H₂₇—Ph—* Compound 53 S Sp-C₁₄H₂₉—Ph—* p-C₁₄H₂₉—Ph—* p-C₁₄H₂₉—Ph—* p-C₁₄H₂₉—Ph—* Compound 54 S Sp-C₁₅H₃₁—Ph—* p-C₁₅H₃₁—Ph—* p-C₁₅H₃₁—Ph—* p-C₁₅H₃₁—Ph—* Compound 55 S Sp-C₁₆H₃₃—Ph—* p-C₁₆H₃₃—Ph—* p-C₁₆H₃₃—Ph—* p-C₁₆H₃₃—Ph—* Compound 56 S Sp-C₁₇H₃₅—Ph—* p-C₁₇H₃₅—Ph—* p-C₁₇H₃₅—Ph—* p-C₁₇H₃₅—Ph—* Compound 57 S Sp-C₁₈H₃₇—Ph—* p-C₁₈H₃₇—Ph—* p-C₁₈H₃₇—Ph—* p-C₁₈H₃₇—Ph—* Compound 58 S S

H

H Compound 59 S S

H

H Compound 60 S S

H

H Compound 61 S S

H

H Compound 62 S S

H

H Compound 63 S S

H

H Compound 64 S S

H

H Compound 65 S S

H

H Compound 66 S S

H

H Compound 67 S S

H

H Compound 68 S S

H

H Compound 69 S S

H

H Compound 70 S S

H

H Compound 71 S S

H

H Compound 72 S S

H

H Compound 73 S S

H

H

TABLE 3 X^(a1) X^(a2) R^(a11) R^(a12) R^(a21) R^(a22) Compound 74 S S

H

H Compound 75 S S

H

H Compound 76 S S

H

H Compound 77 S S

H

H Compound 78 S S

H

H Compound 79 S S

H

H Compound 80 S S

H

H Compound 81 S S

H

H Compound 82 S S

H

H Compound 83 S S

H

H Compound 84 S S

H

H Compound 85 S S

H

H Compound 86 S S

Compound 87 S S

Compound 88 S S

Compound 89 S S

Compound 90 S S

Compound 91 S S

TABLE 4 X^(a1) X^(a2) R^(a11) R^(a12) R^(a21) R^(a22) Compound 92  S S

Compound 93  S S

Compound 94  S S

Compound 95  S S

Compound 96  S S

Compound 97  S S

Compound 98  S S

Compound 99  S S

Compound 100 S S

H

H Compound 101 S S

H

H Compound 102 S S

H

H Compound 103 S S

H

H Compound 104 S S

H

H Compound 105 S S

H

H Compound 106 S S

H

H Compound 107 S S

H

H Compound 108 S S

H

H Compound 109 S S

H

H

TABLE 5 X^(a1) X^(a2) R^(a11) R^(a12) R^(a21) R^(a22) Compound 110 S S

H

H Compound 111 S S

H

H Compound 112 S S

H

H Compound 113 S S

H

H Compound 114 S S

Compound 115 S S

Compound 116 S S

Compound 117 S S

Compound 118 S S

Compound 119 S S

Compound 120 S S

Compound 121 S S

Compound 122 S S

Compound 123 S S

Compound 124 S S

Compound 125 S S

Compound 126 S S

Compound 127 S S

TABLE 6 X^(a1) X^(a2) R^(a11) R^(a12) R^(a21) R^(a22) Compound 128 S S HC₅H₁₁—* H C₅H₁₁—* Compound 129 S S H C₆H₁₃—* H C₆H₁₃—* Compound 130 S SH C₇H₁₅—* H C₇H₁₅—* Compound 131 S S H C₈H₁₇—* H C₈H₁₇—* Compound 132 SS H C₉H₁₉—* H C₉H₁₉—* Compound 133 S S H C₁₀H₂₁—* H C₁₀H₂₁—* Compound134 S S H C₁₁H₂₃—* H C₁₁H₂₃—* Compound 135 S S H C₁₂H₂₅—* H C₁₂H₂₅—*Compound 136 S S H C₁₃H₂₇—* H C₁₃H₂₇—* Compound 137 S S H C₁₄H₂₉—* HC₁₄H₂₉—* Compound 138 S S H C₁₅H₃₁—* H C₁₅H₃₁—* Compound 139 S S HC₁₆H₃₃—* H C₁₆H₃₃—* Compound 140 S S H C₁₇H₃₅—* H C₁₇H₃₅—* Compound 141S S H C₁₈H₃₇—* H C₁₈H₃₇—* Compound 142 S S H p-C₅H₁₁—Ph—* H p-C₅H₁₁—Ph—*Compound 143 S S H p-C₆H₁₃—Ph—* H p-C₆H₁₃—Ph—* Compound 144 S S Hp-C₇H₁₅—Ph—* H p-C₇H₁₅—Ph—* Compound 145 S S H p-C₈H₁₇—Ph—* Hp-C₈H₁₇—Ph—* Compound 146 S S H p-C₉H₁₉—Ph—* H p-C₉H₁₉—Ph—* Compound 147S S H p-C₁₀H₂₁—Ph—* H p-C₁₀H₂₁—Ph—* Compound 148 S S H p-C₁₁H₂₃—Ph—* Hp-C₁₁H₂₃—Ph—* Compound 149 S S H p-C₁₂H₂₅—Ph—* H p-C₁₂H₂₅—Ph—* Compound150 S S H p-C₁₃H₂₇—Ph—* H p-C₁₃H₂₇—Ph—* Compound 151 S S H p-C₁₄H₂₉—Ph—*H p-C₁₄H₂₉—Ph—* Compound 152 S S H p-C₁₅H₃₁—Ph—* H p-C₁₅H₃₁—Ph—*Compound 153 S S H p-C₁₆H₃₃—Ph—* H p-C₁₆H₃₃—Ph—* Compound 154 S S Hp-C₁₇H₃₅—Ph—* H p-C₁₇H₃₅—Ph—* Compound 155 S S H p-C₁₈H₃₇—Ph—* Hp-C₁₈H₃₇—Ph—* Compound 156 S S H

H

Compound 157 S S H

H

Compound 158 S S H

H

Compound 159 S S H

H

Compound 160 S S H

H

Compound 161 S S H

H

Compound 162 S S H

H

Compound 163 S S H

H

TABLE 7 X^(a1) X^(a2) R^(a11) R^(a12) R^(a21) R^(a22) Compound 164 S S H

H

Compound 165 S S H

H

Compound 166 S S H

H

Compound 167 S S H

H

Compound 168 S S H

H

Compound 169 S S H

H

Compound 170 S S H H C₅H₁₁—* H Compound 171 S S H H C₆H₁₃—* H Compound172 S S H H C₇H₁₅—* H Compound 173 S S H H C₈H₁₇—* H Compound 174 S S HH C₉H₁₉—* H Compound 175 S S H H C₁₀H₂₁—* H Compound 176 S S H HC₁₁H₂₃—* H Compound 177 S S H H C₁₂H₂₅—* H Compound 178 S S H H C₁₃H₂₇—*H Compound 179 S S H H C₁₄H₂₉—* H Compound 180 S S H H C₁₅H₃₁—* HCompound 181 S S H H C₁₆H₃₃—* H Compound 182 S S H H C₁₇H₃₅—* H Compound183 S S H H C₁₈H₃₇—* H Compound 184 S S Ph H C₅H₁₁—* H Compound 185 S SPh H C₆H₁₃—* H Compound 186 S S Ph H C₇H₁₅—* H Compound 187 S S Ph HC₈H₁₇—* H Compound 188 S S Ph H C₉H₁₉—* H Compound 189 S S Ph H C₁₀H₂₁—*H Compound 190 S S Ph H C₁₁H₂₃—* H Compound 191 S S Ph H C₁₂H₂₅—* HCompound 192 S S Ph H C₁₃H₂₇—* H Compound 193 S S Ph H C₁₄H₂₉—* HCompound 194 S S Ph H C₁₅H₃₁—* H Compound 195 S S Ph H C₁₆H₃₃—* HCompound 196 S S Ph H C₁₇H₃₅—* H Compound 197 S S Ph H C₁₈H₃₇—* HCompound 198 S S

H C₅H₁₁—* H Compound 199 S S

H C₆H₁₃—* H

TABLE 8 X^(a1) X^(a2) R^(a11) R^(a12) R^(a21) R^(a22) Compound 200 S S

H C₇H₁₅—* H Compound 201 S S

H C₈H₁₇—* H Compound 202 S S

H C₉H₁₉—* H Compound 203 S S

H C₁₀H₂₁—* H Compound 204 S S

H C₁₁H₂₃—* H Compound 205 S S

H C₁₂H₂₅—* H Compound 206 S S

H C₁₃H₂₇—* H Compound 207 S S

H C₁₄H₂₉—* H Compound 208 S S

H C₁₅H₃₁—* H Compound 209 S S

H C₁₆H₃₃—* H Compound 210 S S

H C₁₇H₃₅—* H Compound 211 S S

H C₁₈H₃₇—* H Compound 212 S S H H H C₅H₁₁—* Compound 213 S S H H HC₆H₁₃—* Compound 214 S S H H H C₇H₁₅—* Compound 215 S S H H H C₈H₁₇—*Compound 216 S S H H H C₉H₁₉—* Compound 217 S S H H H C₁₀H₂₁—* Compound218 S S H H H C₁₁H₂₃—* Compound 219 S S H H H C₁₂H₂₅—* Compound 220 S SH H H C₁₃H₂₇—* Compound 221 S S H H H C₁₄H₂₉—* Compound 222 S S H H HC₁₅H₃₁—* Compound 223 S S H H H C₁₆H₃₃—* Compound 224 S S H H H C₁₇H₃₅—*Compound 225 S S H H H C₁₈H₃₇—* Compound 226 S S H H p-C₅H₁₁—Ph—* HCompound 227 S S H H p-C₆H₁₃—Ph—* H Compound 228 S S H H p-C₇H₁₅—Ph—* HCompound 229 S S H H p-C₈H₁₇—Ph—* H Compound 230 S S H H p-C₉H₁₉—Ph—* H

TABLE 9 X^(a1) X^(a2) R^(a11) R^(a12) R^(a21) R^(a22) Compound 231 S S HH p-C₁₀H₂₁—Ph—* H Compound 232 S S H H p-C₁₁H₂₃—Ph—* H Compound 233 S SH H p-C₁₂H₂₅—Ph—* H Compound 234 S S H H p-C₁₃H₂₇—Ph—* H Compound 235 SS H H p-C₁₄H₂₉—Ph—* H Compound 236 S S H H p-C₁₅H₃₁—Ph—* H Compound 237S S H H p-C₁₆H₃₃—Ph—* H Compound 238 S S H H p-C₁₇H₃₅—Ph—* H Compound239 S S H H p-C₁₈H₃₇—Ph—* H Compound 240 S S Ph H p-C₅H₁₁—Ph—* HCompound 241 S S Ph H p-C₆H₁₃—Ph—* H Compound 242 S S Ph H p-C₇H₁₅—Ph—*H Compound 243 S S Ph H p-C₈H₁₇—Ph—* H Compound 244 S S Ph Hp-C₉H₁₉—Ph—* H Compound 245 S S Ph H p-C₁₀H₂₁—Ph—* H Compound 246 S S PhH p-C₁₁H₂₃—Ph—* H Compound 247 S S Ph H p-C₁₂H₂₅—Ph—* H Compound 248 S SPh H p-C₁₃H₂₇—Ph—* H Compound 249 S S Ph H p-C₁₄H₂₉—Ph—* H Compound 250S S Ph H p-C₁₅H₃₁—Ph—* H Compound 251 S S Ph H p-C₁₆H₃₃—Ph—* H Compound252 S S Ph H p-C₁₇H₃₅—Ph—* H Compound 253 S S Ph H p-C₁₈H₃₇—Ph—* HCompound 254 S S

H p-C₅H₁₁—Ph—* H Compound 255 S S

H p-C₆H₁₃—Ph—* H Compound 256 S S

H p-C₇H₁₅—Ph—* H Compound 257 S S

H p-C₈H₁₇—Ph—* H Compound 258 S S

H p-C₉H₁₉—Ph—* H Compound 259 S S

H p-C₁₀H₂₁—Ph—* H Compound 260 S S

H p-C₁₁H₂₃—Ph—* H Compound 261 S S

H p-C₁₂H₂₅—Ph—* H Compound 262 S S

H p-C₁₃H₂₇—Ph—* H Compound 263 S S

H p-C₁₄H₂₉—Ph—* H

TABLE 10 X^(a1) X^(a2) R^(a11) R^(a12) R^(a21) R^(a22) Compound 264 S S

H p-C₁₅H₃₁—Ph—* H Compound 265 S S

H p-C₁₆H₃₃—Ph—* H Compound 266 S S

H p-C₁₇H₃₅—Ph—* H Compound 267 S S

H p-C₁₈H₃₇—Ph—* H Compound 268 S S H H H p-C₅H₁₁—Ph—* Compound 269 S S HH H p-C₆H₁₃—Ph—* Compound 270 S S H H H p-C₇H₁₅—Ph—* Compound 271 S S HH H p-C₈H₁₇—Ph—* Compound 272 S S H H H p-C₉H₁₉—Ph—* Compound 273 S S HH H p-C₁₀H₂₁—Ph—* Compound 274 S S H H H p-C₁₁H₂₃—Ph—* Compound 275 S SH H H p-C₁₂H₂₅—Ph—* Compound 276 S S H H H p-C₁₃H₂₇—Ph—* Compound 277 SS H H H p-C₁₄H₂₉—Ph—* Compound 278 S S H H H p-C₁₅H₃₁—Ph—* Compound 279S S H H H p-C₁₆H₃₃—Ph—* Compound 280 S S H H H p-C₁₇H₃₅—Ph—* Compound281 S S H H H p-C₁₈H₃₇—Ph—* Compound 282 S S H H

H Compound 283 S S H H

H Compound 284 S S H H

H Compound 285 S S H H

H Compound 286 S S H H

H Compound 287 S S H H

H Compound 288 S S H H

H Compound 289 S S H H

H Compound 290 S S H H

H

TABLE 11 X^(a1) X^(a2) R^(a11) R^(a12) R^(a21) R^(a22) Com- pound 291 SS H H

H Com- pound 292 S S H H

H Com- pound 293 S S H H

H Com- pound 294 S S H H

H Com- pound 295 S S Ph H

H Com- pound 296 S S Ph H

H Com- pound 297 S S Ph H

H Com- pound 298 S S Ph H

H Com- pound 299 S S Ph H

H Com- pound 300 S S Ph H

H Com- pound 301 S S Ph H

H Com- pound 302 S S Ph H

H Com- pound 303 S S Ph H

H Com- pound 304 S S Ph H

H Com- pound 305 S S Ph H

H Com- pound 306 S S Ph H

H Com- pound 307 S S Ph H

H Com- pound 308 S S

H

H

TABLE 12 X^(a1) X^(a2) R^(a11) R^(a12) R^(a21) R^(a22) Compound 309 S S

H

H Compound 310 S S

H

H Compound 311 S S

H

H Compound 312 S S

H

H Compound 313 S S

H

H Compound 314 S S

H

H Compound 315 S S

H

H Compound 316 S S

H

H Compound 317 S S

H

H Compound 318 S S

H

H Compound 319 S S

H

H Compound 320 S S

H

H Compound 321 S S H H H

Compound 322 S S H H H

Compound 323 S S H H H

Compound 324 S S H H H

Compound 325 S S H H H

Compound 326 S S H H H

TABLE 13 X^(a1) X^(a2) R^(a11) R^(a12) R^(a21) R^(a22) Compound 327 S SH H H

Compound 328 S S H H H

Compound 329 S S H H H

Compound 330 S S H H H

Compound 331 S S H H H

Compound 332 S S H H H

Compound 333 S S H H H

Compound 334 S S H H

H Compound 335 S S H H

H Compound 336 S S H H

H Compound 337 S S H H

H Compound 338 S S H H

H Compound 339 S S H H

H Compound 340 S S H H

H Compound 341 S S H H

H Compound 342 S S H H

H Compound 343 S S H H

H Compound 344 S S H H

H

TABLE 14 X^(a1) X^(a2) R^(a11) R^(a12) R^(a21) R^(a22) Compound 345 S SH H

H Compound 346 S S H H

H Compound 347 S S H H

H Compound 348 S S Ph H

H Compound 349 S S Ph H

H Compound 350 S S Ph H

H Compound 351 S S Ph H

H Compound 352 S S Ph H

H Compound 353 S S Ph H

H Compound 354 S S Ph H

H Compound 355 S S Ph H

H Compound 356 S S Ph H

H Compound 357 S S Ph H

H Compound 358 S S Ph H

H Compound 359 S S Ph H

H Compound 360 S S Ph H

H Compound 361 S S Ph H

H Compound 362 S S

H

H

TABLE 15 X^(a1) X^(a2) R^(a11) R^(a12) R^(a21) R^(a22) Compound 363 S S

H

H Compound 364 S S

H

H Compound 365 S S

H

H Compound 366 S S

H

H Compound 367 S S

H

H Compound 368 S S

H

H Compound 369 S S

H

H Compound 370 S S

H

H Compound 371 S S

H

H Compound 372 S S

H

H Compound 373 S S

H

H Compound 374 S S

H

H Compound 375 S S

H

H Compound 376 S S C₁₀H₂₁—* H p-C₅H₁₁—Ph—* H Compound 377 S S C₁₀H₂₁—* Hp-C₆H₁₃—Ph—* H Compound 378 S S C₁₀H₂₁—* H p-C₇H₁₅—Ph—* H Compound 379 SS C₁₀H₂₁—* H p-C₈H₁₇—Ph—* H Compound 380 S S C₁₀H₂₁—* H p-C₉H₁₉—Ph—* HCompound 381 S S C₁₀H₂₁—* H p-C₁₀H₂₁—Ph—* H Compound 382 S S C₁₀H₂₁—* Hp-C₁₁H₂₃—Ph—* H Compound 383 S S C₁₀H₂₁—* H p-C₁₂H₂₅—Ph—* H Compound 384S S C₁₀H₂₁—* H p-C₁₃H₂₇—Ph—* H Compound 385 S S C₁₀H₂₁—* H p-C₁₄H₂₉—Ph—*H Compound 386 S S C₁₀H₂₁—* H p-C₁₅H₃₁—Ph—* H Compound 387 S S C₁₀H₂₁—*H p-C₁₆H₃₃—Ph—* H Compound 388 S S C₁₀H₂₁—* H p-C₁₇H₃₅—Ph—* H Compound389 S S C₁₀H₂₁—* H p-C₁₈H₃₇—Ph—* H

TABLE 16 X^(a1) X^(a2) R^(a11) R^(a12) R^(a21) R^(a22) Compound 390 S SC₁₂H₂₅—* H

H Compound 391 S S C₁₂H₂₅—* H

H Compound 392 S S C₁₂H₂₅—* H

H Compound 393 S S C₁₂H₂₅—* H

H Compound 394 S S C₁₂H₂₅—* H

H Compound 395 S S C₁₂H₂₅—* H

H Compound 396 S S C₁₂H₂₅—* H

H Compound 397 S S C₁₂H₂₅—* H

H Compound 398 S S C₁₂H₂₅—* H

H Compound 399 S S C₁₂H₂₅—* H

H Compound 400 S S C₁₂H₂₅—* H

H Compound 401 S S C₁₂H₂₅—* H

H Compound 402 S S C₁₂H₂₅—* H

H Compound 403 S S C₁₂H₂₅—* H

H Compound 404 S S C₅H₁₁—* H H C₁₂H₂₅—* Compound 405 S S C₆H₁₃—* H HC₁₂H₂₅—* Compound 406 S S C₇H₁₅—* H H C₁₂H₂₅—* Compound 407 S S C₈H₁₇—*H H C₁₂H₂₅—* Compound 408 S S C₉H₁₉—* H H C₁₂H₂₅—* Compound 409 S SC₁₀H₂₁—* H H C₁₂H₂₅—* Compound 410 S S C₁₁H₂₃—* H H C₁₂H₂₅—* Compound411 S S C₁₂H₂₅—* H H C₁₂H₂₅—* Compound 412 S S C₁₃H₂₇—* H H C₁₂H₂₅—*Compound 413 S S C₁₄H₂₉—* H H C₁₂H₂₅—* Compound 414 S S C₁₅H₃₁—* H HC₁₂H₂₅—* Compound 415 S S C₁₆H₃₃—* H H C₁₂H₂₅—* Compound 416 S SC₁₇H₃₅—* H H C₁₂H₂₅—* Compound 417 S S C₁₈H₃₇—* H H C₁₂H₂₅—*

TABLE 17 X^(a1) X^(a2) R^(a11) R^(a12) R^(a21) R^(a22) Compound 418 S SC₁₀H₂₁—* H H p-C₅H₁₁—Ph—* Compound 419 S S C₁₀H₂₁—* H H p-C₆H₁₃—Ph—*Compound 420 S S C₁₀H₂₁—* H H p-C₇H₁₅—Ph—* Compound 421 S S C₁₀H₂₁—* H Hp-C₈H₁₇—Ph—* Compound 422 S S C₁₀H₂₁—* H H p-C₉H₁₉—Ph—* Compound 423 S SC₁₀H₂₁—* H H p-C₁₀H₂₁—Ph—* Compound 424 S S C₁₀H₂₁—* H H p-C₁₁H₂₃—Ph—*Compound 425 S S C₁₀H₂₁—* H H p-C₁₂H₂₅—Ph—* Compound 426 S S C₁₀H₂₁—* HH p-C₁₃H₂₇—Ph—* Compound 427 S S C₁₀H₂₁—* H H p-C₁₄H₂₉—Ph—* Compound 428S S C₁₀H₂₁—* H H p-C₁₅H₃₁—Ph—* Compound 429 S S C₁₀H₂₁—* H Hp-C₁₆H₃₃—Ph—* Compound 430 S S C₁₀H₂₁—* H H p-C₁₇H₃₅—Ph—* Compound 431 SS C₁₀H₂₁—* H H p-C₁₈H₃₇—Ph—* Compound 432 S S H C₁₀H₂₁—* H p-C₅H₁₁—Ph—*Compound 433 S S H C₁₀H₂₁—* H p-C₆H₁₃—Ph—* Compound 434 S S H C₁₀H₂₁—* Hp-C₇H₁₅—Ph—* Compound 435 S S H C₁₀H₂₁—* H p-C₈H₁₇—Ph—* Compound 436 S SH C₁₀H₂₁—* H p-C₉H₁₉—Ph—* Compound 437 S S H C₁₀H₂₁—* H p-C₁₀H₂₁—Ph—*Compound 438 S S H C₁₀H₂₁—* H p-C₁₁H₂₃—Ph—* Compound 439 S S H C₁₀H₂₁—*H p-C₁₂H₂₅—Ph—* Compound 440 S S H C₁₀H₂₁—* H p-C₁₃H₂₇—Ph—* Compound 441S S H C₁₀H₂₁—* H p-C₁₄H₂₉—Ph—* Compound 442 S S H C₁₀H₂₁—* Hp-C₁₅H₃₁—Ph—* Compound 443 S S H C₁₀H₂₁—* H p-C₁₆H₃₃—Ph—* Compound 444 SS H C₁₀H₂₁—* H p-C₁₇H₃₅—Ph—* Compound 445 S S H C₁₀H₂₁—* H p-C₁₈H₃₇—Ph—*Compound 446 S S

H

H Compound 447 S S

H

H Compound 448 S S

H

H Compound 449 S S

H

H Compound 450 S S

H

H Compound 451 S S

H

H Compound 452 S S

H

H Compound 453 S S

H

H

TABLE 18 X^(a1) X^(a2) R^(a11) R^(a12) R^(a21) R^(a22) Compound 454 S S

H

H Compound 455 S S

H

H Compound 456 S S

H

H Compound 457 S S

H

H Compound 458 S S

H

H Compound 459 S S

H

H Compound 460 S S

H

H Compound 461 S S

H

H Compound 462 S S

H

H Compound 463 S S

H

H Compound 464 S S

H

H Compound 465 S S

H

H Compound 466 S S

H

H Compound 467 S S

H

H Compound 468 S S

H

H Compound 469 S S

H

H Compound 470 S S

H

H Compound 471 S S

H

H

TABLE 19 X^(a1) X^(a2) R^(a11) R^(a12) R^(a21) R^(a22) Compound 472 S S

H

H Compound 473 S S

H

H Compound 474 S S

H

H Compound 475 S S

H

H Compound 476 S S

H

H Compound 477 S S

H

H Compound 478 S S

H

H Compound 479 S S

H

H Compound 480 S S

H

H Compound 481 S S

H

H Compound 482 S S

H

H Compound 483 S S

H

H Compound 484 S S

H

H Compound 485 S S

H

H Compound 486 S S

H

H Compound 487 O O C₅H₁₁—* H C₅H₁₁—* H Compound 488 O O C₆H₁₃—* HC₆H₁₃—* H Compound 489 O O C₇H₁₅—* H C₇H₁₅—* H Compound 490 O O C₈H₁₇—*H C₈H₁₇—* H Compound 491 O O C₉H₁₉—* H C₉H₁₉—* H Compound 492 O OC₁₀H₂₁—* H C₁₀H₂₁—* H Compound 493 O O C₁₁H₂₃—* H C₁₁H₂₃—* H Compound494 O O C₁₂H₂₅—* H C₁₂H₂₅—* H Compound 495 O O C₁₃H₂₇—* H C₁₃H₂₇—* HCompound 496 O O C₁₄H₂₉—* H C₁₄H₂₉—* H Compound 497 O O C₁₅H₃₁—* HC₁₅H₃₁—* H

TABLE 20 X^(a1) X^(a2) R^(a11) R^(a12) R^(a21) R^(a22) Compound 498 O OC₁₆H₃₃—* H C₁₆H₃₃—* H Compound 499 O O C₁₇H₃₅—* H C₁₇H₃₅—* H Compound500 O O C₁₈H₃₇—* H C₁₈H₃₇—* H Compound 501 O O p-C₅H₁₁—Ph—* Hp-C₅H₁₁—Ph—* H Compound 502 O O p-C₆H₁₃—Ph—* H p-C₆H₁₃—Ph—* H Compound503 O O p-C₇H₁₅—Ph—* H p-C₇H₁₅—Ph—* H Compound 504 O O p-C₈H₁₇—Ph—* Hp-C₈H₁₇—Ph—* H Compound 505 O O p-C₉H₁₉—Ph—* H p-C₉H₁₉—Ph—* H Compound506 O O p-C₁₀H₂₁—Ph—* H p-C₁₀H₂₁—Ph—* H Compound 507 O O p-C₁₁H₂₃—Ph—* Hp-C₁₁H₂₃—Ph—* H Compound 508 O O p-C₁₂H₂₅—Ph—* H p-C₁₂H₂₅—Ph—* HCompound 509 O O p-C₁₃H₂₇—Ph—* H p-C₁₃H₂₇—Ph—* H Compound 510 O Op-C₁₄H₂₉—Ph—* H p-C₁₄H₂₉—Ph—* H Compound 511 O O p-C₁₅H₃₁—Ph—* Hp-C₁₅H₃₁—Ph—* H Compound 512 O O p-C₁₆H₃₃—Ph—* H p-C₁₆H₃₃—Ph—* HCompound 513 O O p-C₁₇H₃₅—Ph—* H p-C₁₇H₃₅—Ph—* H Compound 514 O Op-C₁₈H₃₇—Ph—* H p-C₁₈H₃₇—Ph—* H Compound 515 O O

H

H Compound 516 O O

H

H Compound 517 O O

H

H Compound 518 O O

H

H Compound 519 O O

H

H Compound 520 O O

H

H Compound 521 O O

H

H Compound 522 O O

H

H Compound 523 O O

H

H Compound 524 O O

H

H Compound 525 O O

H

H Compound 526 O O

H

H

TABLE 21 X^(a1) X^(a2) R^(a11) R^(a12) R^(a21) R^(a22) Compound 527 O O

H

H Compound 528 O O

H

H Compound 529 S S C₄H₉OC₄H₈—* H C₄H₉OC₄H₈—* H Compound 530 S SC₂H₅OC₂H₄—* H C₂H₅OC₂H₄—* H Compound 531 S S C₆H₁₃OC₄H₈—* H C₆H₁₃OC₄H₈—*H Compound 532 S S C₂H₅OC₄H₈—* H C₂H₅OC₄H₈—* H Compound 533 S SCH₃OC₃H₆—* H CH₃OC₃H₆—* H Compound 534 S S

H

H Compound 535 S S

H

H Compound 536 S S

H

H Compound 537 S S PhC₃H₆—* H PhC₃H₆—* H Compound 538 S S PhOC₃H₆—* HPhOC₃H₆—* H Compound 539 S S

H

H Compound 540 S S

H

H Compound 541 S S

H

H Compound 542 S S

H

H Compound 543 S S

H

H Compound 544 S S 3,7-Dimethyloctyl H 3,7-Dimethyloctyl H

TABLE 22 X^(a1) X^(a2) R^(a11) R^(a12) R^(a21) R^(a22) Compound S S3,7-Dimethyloctyl H H H 545 Compound S S 2-Ethylhexyl H 2-Ethylhexyl H546 Compound 547 S S

H

H Compound 548 S S

H

H Compound 549 S S

H

H Compound 550 S S

H H H Compound 551 S S

H

H Compound 552 S S C₅H₁₁—* H

H Compound 553 S S

H

H Compound 554 S S

H

H Compound 555 S S

H

H Compound 556 S S

H

H Compound 557 S S

H

H Compound 558 S S

H H H Compound 559 S S

H

H Compound 560 S S

H

H Compound 561 S S

H

H Compound 562 S S

H

H

TABLE 23 X^(b1) X^(b2) R^(b11) R^(b12) R^(b21) R^(b22) Compound 563 S SC₅H₁₁—* H C₅H₁₁—* H Compound 564 S S C₆H₁₃—* H C₆H₁₃—* H Compound 565 SS C₇H₁₅—* H C₇H₁₅—* H Compound 566 S S C₈H₁₇—* H C₈H₁₇—* H Compound 567S S C₉H₁₉—* H C₉H₁₉—* H Compound 568 S S C₁₀H₂₁—* H C₁₀H₂₁—* H Compound569 S S C₁₁H₂₃—* H C₁₁H₂₃—* H Compound 570 S S C₁₂H₂₅—* H C₁₂H₂₅—* HCompound 571 S S C₁₃H₂₇—* H C₁₃H₂₇—* H Compound 572 S S C₁₄H₂₉—* HC₁₄H₂₉—* H Compound 573 S S C₁₅H₃₁—* H C₁₅H₃₁—* H Compound 574 S SC₁₆H₃₃—* H C₁₆H₃₃—* H Compound 575 S S C₁₇H₃₅—* H C₁₇H₃₅—* H Compound576 S S C₁₈H₃₇—* H C₁₈H₃₇—* H Compound 577 S S C₅H₁₁—* C₅H₁₁—* C₅H₁₁—*C₅H₁₁—* Compound 578 S S C₆H₁₃—* C₆H₁₃—* C₆H₁₃—* C₆H₁₃—* Compound 579 SS C₇H₁₅—* C₇H₁₅—* C₇H₁₅—* C₇H₁₅—* Compound 580 S S C₈H₁₇—* C₈H₁₇—*C₈H₁₇—* C₈H₁₇—* Compound 581 S S C₉H₁₉—* C₉H₁₉—* C₉H₁₉—* C₉H₁₉—*Compound 582 S S C₁₀H₂₁—* C₁₀H₂₁—* C₁₀H₂₁—* C₁₀H₂₁—* Compound 583 S SC₁₁H₂₃—* C₁₁H₂₃—* C₁₁H₂₃—* C₁₁H₂₃—* Compound 584 S S C₁₂H₂₅—* C₁₂H₂₅—*C₁₂H₂₅—* C₁₂H₂₅—* Compound 585 S S C₁₃H₂₇—* C₁₃H₂₇—* C₁₃H₂₇—* C₁₃H₂₇—*Compound 586 S S C₁₄H₂₉—* C₁₄H₂₉—* C₁₄H₂₉—* C₁₄H₂₉—* Compound 587 S SC₁₅H₃₁—* C₁₅H₃₁—* C₁₅H₃₁—* C₁₅H₃₁—* Compound 588 S S C₁₆H₃₃—* C₁₆H₃₃—*C₁₆H₃₃—* C₁₆H₃₃—* Compound 589 S S C₁₇H₃₅—* C₁₇H₃₅—* C₁₇H₃₅—* C₁₇H₃₅—*Compound 590 S S C₁₈H₃₇—* C₁₈H₃₇—* C₁₈H₃₇—* C₁₈H₃₇—* Compound 591 S Sp-C₅H₁₁—Ph—* H p-C₅H₁₁—Ph—* H Compound 592 S S p-C₆H₁₃—Ph—* Hp-C₆H₁₃—Ph—* H Compound 593 S S p-C₇H₁₅—Ph—* H p-C₇H₁₅—Ph—* H Compound594 S S p-C₈H₁₇—Ph—* H p-C₈H₁₇—Ph—* H Compound 595 S S p-C₉H₁₉—Ph—* Hp-C₉H₁₉—Ph—* H Compound 596 S S p-C₁₀H₂₁—Ph—* H p-C₁₀H₂₁—Ph—* H Compound597 S S p-C₁₁H₂₃—Ph—* H p-C₁₁H₂₃—Ph—* H Compound 598 S S p-C₁₂H₂₅—Ph—* Hp-C₁₂H₂₅—Ph—* H Compound 599 S S p-C₁₃H₂₇—Ph—* H p-C₁₃H₂₇—Ph—* HCompound 600 S S p-C₁₄H₂₉—Ph—* H p-C₁₄H₂₉—Ph—* H Compound 601 S Sp-C₁₅H₃₁—Ph—* H p-C₁₅H₃₁—Ph—* H Compound 602 S S p-C₁₆H₃₃—Ph—* Hp-C₁₆H₃₃—Ph—* H Compound 603 S S p-C₁₇H₃₅—Ph—* H p-C₁₇H₃₅—Ph—* HCompound 604 S S p-C₁₈H₃₇—Ph—* H p-C₁₈H₃₇—Ph—* H Compound 605 S Sp-C₅H₁₁—Ph—* p-C₅H₁₁—Ph—* p-C₅H₁₁—Ph—* p-C₅H₁₁—Ph—* Compound 606 S Sp-C₆H₁₃—Ph—* p-C₆H₁₃—Ph—* p-C₆H₁₃—Ph—* p-C₆H₁₃—Ph—* Compound 607 S Sp-C₇H₁₅—Ph—* p-C₇H₁₅—Ph—* p-C₇H₁₅—Ph—* p-C₇H₁₅—Ph—* Compound 608 S Sp-C₈H₁₇—Ph—* p-C₈H₁₇—Ph—* p-C₈H₁₇—Ph—* p-C₈H₁₇—Ph—* Compound 609 S Sp-C₉H₁₉—Ph—* p-C₉H₁₉—Ph—* p-C₉H₁₉—Ph—* p-C₉H₁₉—Ph—* Compound 610 S Sp-C₁₀H₂₁—Ph—* p-C₁₀H₂₁—Ph—* p-C₁₀H₂₁—Ph—* p-C₁₀H₂₁—Ph—* Compound 611 S Sp-C₁₁H₂₃—Ph—* p-C₁₁H₂₃—Ph—* p-C₁₁H₂₃—Ph—* p-C₁₁H₂₃—Ph—* Compound 612 S Sp-C₁₂H₂₅—Ph—* p-C₁₂H₂₅—Ph—* p-C₁₂H₂₅—Ph—* p-C₁₂H₂₅—Ph—* Compound 613 S Sp-C₁₃H₂₇—Ph—* p-C₁₃H₂₇—Ph—* p-C₁₃H₂₇—Ph—* p-C₁₃H₂₇—Ph—*

TABLE 24 X^(a1) X^(a2) R^(a11) R^(a12) R^(a21) R^(a22) Compound 614 S Sp-C₁₄H₂₉—Ph—* p-C₁₄H₂₉—Ph—* p-C₁₄H₂₉—Ph—* p-C₁₄H₂₉—Ph—* Compound 615 S Sp-C₁₅H₃₁—Ph—* p-C₁₅H₃₁—Ph—* p-C₁₅H₃₁—Ph—* p-C₁₅H₃₁—Ph—* Compound 616 S Sp-C₁₆H₃₃—Ph—* p-C₁₆H₃₃—Ph—* p-C₁₆H₃₃—Ph—* p-C₁₆H₃₃—Ph—* Compound 617 S Sp-C₁₇H₃₅—Ph—* p-C₁₇H₃₅—Ph—* p-C₁₇H₃₅—Ph—* p-C₁₇H₃₅—Ph—* Compound 618 S Sp-C₁₈H₃₇—Ph—* p-C₁₈H₃₇—Ph—* p-C₁₈H₃₇—Ph—* p-C₁₈H₃₇—Ph—* Compound 619 S S

H

H Compound 620 S S

H

H Compound 621 S S

H

H Compound 622 S S

H

H Compound 623 S S

H

H Compound 624 S S

H

H Compound 625 S S

H

H Compound 626 S S

H

H Compound 627 S S

H

H Compound 628 S S

H

H Compound 629 S S

H

H Compound 630 S S

H

H Compound 631 S S

H

H Compound 632 S S

H

H Compound 633 S S

Compound 634 S S

Compound 635 S S

TABLE 25 X^(a1) X^(a2) R^(a11) R^(a12) R^(a21) R^(a22) Compound 636 S S

Compound 637 S S

Compound 638 S S

Compound 639 S S

Compound 640 S S

Compound 641 S S

Compound 642 S S

Compound 643 S S

Compound 644 S S

Compound 645 S S

Compound 646 S S

Compound 647 S S

H

H Compound 648 S S

H

H Compound 649 S S

H

H Compound 650 S S

H

H Compound 651 S S

H

H Compound 652 S S

H

H Compound 653 S S

H

H

TABLE 26 X^(a1) X^(a2) R^(a11) R^(a12) R^(a21) R^(a22) Compound 654 S S

H

H Compound 655 S S

H

H Compound 656 S S

H

H Compound 657 S S

H

H Compound 658 S S

H

H Compound 659 S S

H

H Compound 660 S S

H

H Compound 661 S S

Compound 662 S S

Compound 663 S S

Compound 664 S S

Compound 665 S S

Compound 666 S S

Compound 667 S S

Compound 668 S S

Compound 669 S S

Compound 670 S S

Compound 671 S S

TABLE 27 X^(a1) X^(a2) R^(a11) R^(a12) R^(a21) R^(a22) Compound 672 S S

Compound 673 S S

Compound 674 S S

Compound 675 S S H C₅H₁₁—* H C₅H₁₁—* Compound 676 S S H C₆H₁₃—* HC₆H₁₃—* Compound 677 S S H C₇H₁₅—* H C₇H₁₅—* Compound 678 S S H C₈H₁₇—*H C₈H₁₇—* Compound 679 S S H C₉H₁₉—* H C₉H₁₉—* Compound 680 S S HC₁₀H₂₁—* H C₁₀H₂₁—* Compound 681 S S H C₁₁H₂₃—* H C₁₁H₂₃—* Compound 682S S H C₁₂H₂₅—* H C₁₂H₂₅—* Compound 683 S S H C₁₃H₂₇—* H C₁₃H₂₇—*Compound 684 S S H C₁₄H₂₉—* H C₁₄H₂₉—* Compound 685 S S H C₁₅H₃₁—* HC₁₅H₃₁—* Compound 686 S S H C₁₆H₃₃—* H C₁₆H₃₃—* Compound 687 S S HC₁₇H₃₅—* H C₁₇H₃₅—* Compound 688 S S H C₁₈H₃₇—* H C₁₈H₃₇—* Compound 689S S H p-C₅H₁₁—Ph—* H p-C₅H₁₁—Ph—* Compound 690 S S H p-C₆H₁₃—Ph—* Hp-C₆H₁₃—Ph—* Compound 691 S S H p-C₇H₁₅—Ph—* H p-C₇H₁₅—Ph—* Compound 692S S H p-C₈H₁₇—Ph—* H p-C₈H₁₇—Ph—* Compound 693 S S H p-C₉H₁₉—Ph—* Hp-C₉H₁₉—Ph—* Compound 694 S S H p-C₁₀H₂₁—Ph—* H p-C₁₀H₂₁—Ph—* Compound695 S S H p-C₁₁H₂₃—Ph—* H p-C₁₁H₂₃—Ph—* Compound 696 S S H p-C₁₂H₂₅—Ph—*H p-C₁₂H₂₅—Ph—* Compound 697 S S H p-C₁₃H₂₇—Ph—* H p-C₁₃H₂₇—Ph—*Compound 698 S S H p-C₁₄H₂₉—Ph—* H p-C₁₄H₂₉—Ph—* Compound 699 S S Hp-C₁₅H₃₁—Ph—* H p-C₁₅H₃₁—Ph—* Compound 700 S S H p-C₁₆H₃₃—Ph—* Hp-C₁₆H₃₃—Ph—* Compound 701 S S H p-C₁₇H₃₅—Ph—* H p-C₁₇H₃₅—Ph—* Compound702 S S H p-C₁₈H₃₇—Ph—* H p-C₁₈H₃₇—Ph—* Compound 703 S S H

H

Compound 704 S S H

H

Compound 705 S S H

H

Compound 706 S S H

H

Compound 707 S S H

H

TABLE 28 X^(a1) X^(a2) R^(a11) R^(a12) R^(a21) R^(a22) Compound 708 S SH

H

Compound 709 S S H

H

Compound 710 S S H

H

Compound 711 S S H

H

Compound 712 S S H

H

Compound 713 S S H

H

Compound 714 S S H

H

Compound 715 S S H

H

Compound 716 S S H

H

Compound 717 S S H H C₅H₁₁—* H Compound 718 S S H H C₆H₁₃—* H Compound719 S S H H C₇H₁₅—* H Compound 720 S S H H C₈H₁₇—* H Compound 721 S S HH C₉H₁₉—* H Compound 722 S S H H C₁₀H₂₁—* H Compound 723 S S H HC₁₁H₂₃—* H Compound 724 S S H H C₁₂H₂₅—* H Compound 725 S S H H C₁₃H₂₇—*H Compound 726 S S H H C₁₄H₂₉—* H Compound 727 S S H H C₁₅H₃₁—* HCompound 728 S S H H C₁₆H₃₃—* H Compound 729 S S H H C₁₇H₃₅—* H Compound730 S S H H C₁₈H₃₇—* H Compound 731 S S Ph H C₅H₁₁—* H Compound 732 S SPh H C₆H₁₃—* H Compound 733 S S Ph H C₇H₁₅—* H Compound 734 S S Ph HC₈H₁₇—* H Compound 735 S S Ph H C₉H₁₉—* H Compound 736 S S Ph H C₁₀H₂₁—*H Compound 737 S S Ph H C₁₁H₂₃—* H Compound 738 S S Ph H C₁₂H₂₅—* HCompound 739 S S Ph H C₁₃H₂₇—* H Compound 740 S S Ph H C₁₄H₂₉—* HCompound 741 S S Ph H C₁₅H₃₁—* H Compound 742 S S Ph H C₁₆H₃₃—* HCompound 743 S S Ph H C₁₇H₃₅—* H

TABLE 29 X^(a1) X^(a2) R^(a11) R^(a12) R^(a21) R^(a22) Compound 744 S SPh H C₁₈H₃₇—* H Compound 745 S S

H C₅H₁₁—* H Compound 746 S S

H C₆H₁₃—* H Compound 747 S S

H C₇H₁₅—* H Compound 748 S S

H C₈H₁₇—* H Compound 749 S S

H C₉H₁₉—* H Compound 750 S S

H C₁₀H₂₁—* H Compound 751 S S

H C₁₁H₂₃—* H Compound 752 S S

H C₁₂H₂₅—* H Compound 753 S S

H C₁₃H₂₇—* H Compound 754 S S

H C₁₄H₂₉—* H Compound 755 S S

H C₁₅H₃₁—* H Compound 756 S S

H C₁₆H₃₃—* H Compound 757 S S

H C₁₇H₃₅—* H Compound 758 S S

H C₁₈H₃₇—* H Compound 759 S S H H H C₅H₁₁—* Compound 760 S S H H HC₆H₁₃—* Compound 761 S S H H H C₇H₁₅—* Compound 762 S S H H H C₈H₁₇—*Compound 763 S S H H H C₉H₁₉—* Compound 764 S S H H H C₁₀H₂₁—* Compound765 S S H H H C₁₁H₂₃—* Compound 766 S S H H H C₁₂H₂₅—* Compound 767 S SH H H C₁₃H₂₇—* Compound 768 S S H H H C₁₄H₂₉—* Compound 769 S S H H HC₁₅H₃₁—* Compound 770 S S H H H C₁₆H₃₃—* Compound 771 S S H H H C₁₇H₃₅—*

TABLE 30 X^(b1) X^(b2) R^(b11) R^(b12) R^(b21) R^(b22) Compound 772 S SH H H C₁₈H₃₇—* Compound 773 S S H H p-C₅H₁₁—Ph—* H Compound 774 S S H Hp-C₆H₁₃—Ph—* H Compound 775 S S H H p-C₇H₁₅—Ph—* H Compound 776 S S H Hp-C₈H₁₇—Ph—* H Compound 777 S S H H p-C₉H₁₉—Ph—* H Compound 778 S S H Hp-C₁₀H₂₁—Ph—* H Compound 779 S S H H p-C₁₁H₂₃—Ph—* H Compound 780 S S HH p-C₁₂H₂₅—Ph—* H Compound 781 S S H H p-C₁₃H₂₇—Ph—* H Compound 782 S SH H p-C₁₄H₂₉—Ph—* H Compound 783 S S H H p-C₁₅H₃₁—Ph—* H Compound 784 SS H H p-C₁₆H₃₃—Ph—* H Compound 785 S S H H p-C₁₇H₃₅—Ph—* H Compound 786S S H H p-C₁₈H₃₇—Ph—* H Compound 787 S S Ph H p-C₅H₁₁—Ph—* H Compound788 S S Ph H p-C₆H₁₃—Ph—* H Compound 789 S S Ph H p-C₇H₁₅—Ph—* HCompound 790 S S Ph H p-C₈H₁₇—Ph—* H Compound 791 S S Ph H p-C₉H₁₉—Ph—*H Compound 792 S S Ph H p-C₁₀H₂₁—Ph—* H Compound 793 S S Ph Hp-C₁₁H₂₃—Ph—* H Compound 794 S S Ph H p-C₁₂H₂₅—Ph—* H Compound 795 S SPh H p-C₁₃H₂₇—Ph—* H Compound 796 S S Ph H p-C₁₄H₂₉—Ph—* H Compound 797S S Ph H p-C₁₅H₃₁—Ph—* H Compound 798 S S Ph H p-C₁₆H₃₃—Ph—* H Compound799 S S Ph H p-C₁₇H₃₅—Ph—* H Compound 800 S S Ph H p-C₁₈H₃₇—Ph—* HCompound 801 S S

H p-C₅H₁₁—Ph—* H Compound 802 S S

H p-C₆H₁₃—Ph—* H Compound 803 S S

H p-C₇H₁₅—Ph—* H Compound 804 S S

H p-C₈H₁₇—Ph—* H Compound 805 S S

H p-C₉H₁₉—Ph—* H Compound 806 S S

H p-C₁₀H₂₁—Ph—* H Compound 807 S S

H p-C₁₁H₂₃—Ph—* H

TABLE 31 X^(b1) X^(b2) R^(b11) R^(b12) R^(b21) R^(b22) Compound 808 S S

H p-C₁₂H₂₅—Ph—* H Compound 809 S S

H p-C₁₃H₂₇—Ph—* H Compound 810 S S

H p-C₁₄H₂₉—Ph—* H Compound 811 S S

H p-C₁₅H₃₁—Ph—* H Compound 812 S S

H p-C₁₆H₃₃—Ph—* H Compound 813 S S

H p-C₁₇H₃₅—Ph—* H Compound 814 S S

H p-C₁₈H₃₇—Ph—* H Compound 815 S S H H H p-C₅H₁₁—Ph—* Compound 816 S S HH H p-C₆H₁₃—Ph—* Compound 817 S S H H H p-C₇H₁₅—Ph—* Compound 818 S S HH H p-C₈H₁₇—Ph—* Compound 819 S S H H H p-C₉H₁₉—Ph—* Compound 820 S S HH H p-C₁₀H₂₁—Ph—* Compound 821 S S H H H p-C₁₁H₂₃—Ph—* Compound 822 S SH H H p-C₁₂H₂₅—Ph—* Compound 823 S S H H H p-C₁₃H₂₇—Ph—* Compound 824 SS H H H p-C₁₄H₂₉—Ph—* Compound 825 S S H H H p-C₁₅H₃₁—Ph—* Compound 826S S H H H p-C₁₆H₃₃—Ph—* Compound 827 S S H H H p-C₁₇H₃₅—Ph—* Compound828 S S H H H p-C₁₈H₃₇—Ph—* Compound 829 S S H H

H Compound 830 S S H H

H Compound 831 S S H H

H Compound 832 S S H H

H Compound 833 S S H H

H Compound 834 S S H H

H

TABLE 32 X^(b1) X^(b2) R^(b11) R^(b12) R^(b21) R^(b22) Compound 835 S SH H

H Compound 836 S S H H

H Compound 837 S S H H

H Compound 838 S S H H

H Compound 839 S S H H

H Compound 840 S S H H

H Compound 841 S S H H

H Compound 842 S S Ph H

H Compound 843 S S Ph H

H Compound 844 S S Ph H

H Compound 845 S S Ph H

H Compound 846 S S Ph H

H Compound 847 S S Ph H

H Compound 848 S S Ph H

H Compound 849 S S Ph H

H Compound 850 S S Ph H

H Compound 851 S S Ph H

H Compound 852 S S Ph H

H

TABLE 33 X^(b1) X^(b2) R^(b11) R^(b12) R^(b21) R^(b22) Compound 853 S SPh H

H Compound 854 S S Ph H

H Compound 855 S S

H

H Compound 856 S S

H

H Compound 857 S S

H

H Compound 858 S S

H

H Compound 859 S S

H

H Compound 860 S S

H

H Compound 861 S S

H

H Compound 862 S S

H

H Compound 863 S S

H

H Compound 864 S S

H

H Compound 865 S S

H

H Compound 866 S S

H

H Compound 867 S S

H

H Compound 868 S S H H H

Compound 869 S S H H H

Compound 870 S S H H H

TABLE 34 X^(b1) X^(b2) R^(b11) R^(b12) R^(b21) R^(b22) Compound 871 S SH H H

Compound 872 S S H H H

Compound 873 S S H H H

Compound 874 S S H H H

Compound 875 S S H H H

Compound 876 S S H H H

Compound 877 S S H H H

Compound 878 S S H H H

Compound 879 S S H H H

Compound 880 S S H H H

Compound 881 S S H H

H Compound 882 S S H H

H Compound 883 S S H H

H Compound 884 S S H H

H Compound 885 S S H H

H Compound 886 S S H H

H Compound 887 S S H H

H Compound 888 S S H H

H

TABLE 35 X^(b1) X^(b2) R^(b11) R^(b12) R^(b21) R^(b22) Compound 889 S SH H

H Compound 890 S S H H

H Compound 891 S S H H

H Compound 892 S S H H

H Compound 893 S S H H

H Compound 894 S S H H

H Compound 895 S S Ph H

H Compound 896 S S Ph H

H Compound 897 S S Ph H

H Compound 898 S S Ph H

H Compound 899 S S Ph H

H Compound 900 S S Ph H

H Compound 901 S S Ph H

H Compound 902 S S Ph H

H Compound 903 S S Ph H

H Compound 904 S S Ph H

H Compound 905 S S Ph H

H Compound 906 S S Ph H

H

TABLE 36 X^(b1) X^(b2) R^(b11) R^(b12) R^(b21) R^(b22) Compound 907 S SPh H

H Compound 908 S S Ph H

H Compound 909 S S

H

H Compound 910 S S

H

H Compound 911 S S

H

H Compound 912 S S

H

H Compound 913 S S

H

H Compound 914 S S

H

H Compound 915 S S

H

H Compound 916 S S

H

H Compound 917 S S

H

H Compound 918 S S

H

H Compound 919 S S

H

H Compound 920 S S

H

H Compound 921 S S

H

H Compound 922 S S

H

H Compound 923 S S C₁₀H₂₁—* H p-C₅H₁₁—Ph—* H Compound 924 S S C₁₀H₂₁—* Hp-C₆H₁₃—Ph—* H Compound 925 S S C₁₀H₂₁—* H p-C₇H₁₅—Ph—* H Compound 926 SS C₁₀H₂₁—* H p-C₈H₁₇—Ph—* H Compound 927 S S C₁₀H₂₁—* H p-C₉H₁₉—Ph—* HCompound 928 S S C₁₀H₂₁—* H p-C₁₀H₂₁—Ph—* H Compound 929 S S C₁₀H₂₁—* Hp-C₁₁H₂₃—Ph—* H Compound 930 S S C₁₀H₂₁—* H p-C₁₂H₂₅—Ph—* H

TABLE 37 X^(b1) X^(b2) R^(b11) R^(b12) R^(b21) R^(b22) Compound S SC₁₀H₂₁—* H p-C₁₃H₂₇—Ph—* H 931 Compound S S C₁₀H₂₁—* H p-C₁₄H₂₉—Ph—* H932 Compound S S C₁₀H₂₁—* H p-C₁₅H₃₁—Ph—* H 933 Compound S S C₁₀H₂₁—* Hp-C₁₆H₃₃—Ph—* H 934 Compound S S C₁₀H₂₁—* H p-C₁₇H₃₅—Ph—* H 935 CompoundS S C₁₀H₂₁—* H p-C₁₈H₃₇—Ph—* H 936 Compound 937 S S C₁₂H₂₅—* H

H Compound 938 S S C₁₂H₂₅—* H

H Compound 939 S S C₁₂H₂₅—* H

H Compound 940 S S C₁₂H₂₅—* H

H Compound 941 S S C₁₂H₂₅—* H

H Compound 942 S S C₁₂H₂₅—* H

H Compound 943 S S C₁₂H₂₅—* H

H Compound 944 S S C₁₂H₂₅—* H

H Compound 945 S S C₁₂H₂₅-* H

H Compound 946 S S C₁₂H₂₅—* H

H Compound 947 S S C₁₂H₂₅—* H

H Compound 948 S S C₁₂H₂₅—* H

H Compound 949 S S C₁₂H₂₅—* H

H Compound 950 S S C₁₂H₂₅—* H

H Compound S S C₅H₁₁—* H H C₁₂H₂₅—* 951 Compound S S C₆H₁₃—* H HC₁₂H₂₅—* 952 Compound S S C₇H₁₅—* H H C₁₂H₂₅—* 953 Compound S S C₈H₁₇—*H H C₁₂H₂₅—* 954 Compound S S C₉H₁₉—* H H C₁₂H₂₅—* 955 Compound S SC₁₀H₂₁—* H H C₁₂H₂₅—* 956 Compound S S C₁₁H₂₃—* H H C₁₂H₂₅—* 957Compound S S C₁₂H₂₅—* H H C₁₂H₂₅—* 958

TABLE 38 X^(b1) X^(b2) R^(b11) R^(b12) R^(b21) R^(b22) Compound 959 S SC₁₃H₂₇—* H H C₁₂H₂₅—* Compound 960 S S C₁₄H₂₉—* H H C₁₂H₂₅—* Compound961 S S C₁₅H₃₁—* H H C₁₂H₂₅—* Compound 962 S S C₁₆H₃₃—* H H C₁₂H₂₅—*Compound 963 S S C₁₇H₃₅—* H H C₁₂H₂₅—* Compound 964 S S C₁₈H₃₇—* H HC₁₂H₂₅—* Compound 965 S S C₁₀H₂₁—* H H p-C₅H₁₁—Ph—* Compound 966 S SC₁₀H₂₁—* H H p-C₆H₁₃—Ph—* Compound 967 S S C₁₀H₂₁—* H H p-C₇H₁₅—Ph—*Compound 968 S S C₁₀H₂₁—* H H p-C₈H₁₇—Ph—* Compound 969 S S C₁₀H₂₁—* H Hp-C₉H₁₉—Ph—* Compound 970 S S C₁₀H₂₁—* H H p-C₁₀H₂₁—Ph—* Compound 971 SS C₁₀H₂₁—* H H p-C₁₁H₂₃—Ph—* Compound 972 S S C₁₀H₂₁—* H H p-C₁₂H₂₅—Ph—*Compound 973 S S C₁₀H₂₁—* H H p-C₁₃H₂₇—Ph—* Compound 974 S S C₁₀H₂₁—* HH p-C₁₄H₂₉—Ph—* Compound 975 S S C₁₀H₂₁—* H H p-C₁₅H₃₁—Ph—* Compound 976S S C₁₀H₂₁—* H H p-C₁₆H₃₃—Ph—* Compound 977 S S C₁₀H₂₁—* H Hp-C₁₇H₃₅—Ph—* Compound 978 S S C₁₀H₂₁—* H H p-C₁₈H₃₇—Ph—* Compound 979 SS H C₁₀H₂₁—* H p-C₅H₁₁—Ph—* Compound 980 S S H C₁₀H₂₁—* H p-C₆H₁₃—Ph—*Compound 981 S S H C₁₀H₂₁—* H p-C₇H₁₅—Ph—* Compound 982 S S H C₁₀H₂₁—* Hp-C₈H₁₇—Ph—* Compound 983 S S H C₁₀H₂₁—* H p-C₉H₁₉—Ph—* Compound 984 S SH C₁₀H₂₁—* H p-C₁₀H₂₁—Ph—* Compound 985 S S H C₁₀H₂₁—* H p-C₁₁H₂₃—Ph—*Compound 986 S S H C₁₀H₂₁—* H p-C₁₂H₂₅—Ph—* Compound 987 S S H C₁₀H₂₁—*H p-C₁₃H₂₇—Ph—* Compound 988 S S H C₁₀H₂₁—* H p-C₁₄H₂₉—Ph—* Compound 989S S H C₁₀H₂₁—* H p-C₁₅H₃₁—Ph—* Compound 990 S S H C₁₀H₂₁—* Hp-C₁₆H₃₃—Ph—* Compound 991 S S H C₁₀H₂₁—* H p-C₁₇H₃₅—Ph—* Compound 992 SS H C₁₀H₂₁—* H p-C₁₈H₃₇—Ph—* Compound 993 S S

H

H Compound 994 S S

H

H Compound 995 S S

H

H Compound 996 S S

H

H Compound 997 S S

H

H Compound 998 S S

H

H

TABLE 39 X^(b1) X^(b2) R^(b11) R^(b12) R^(b21) R^(b22) Compound 999  S S

H

H Compound 1000 S S

H

H Compound 1001 S S

H

H Compound 1002 S S

H

H Compound 1003 S S

H

H Compound 1004 S S

H

H Compound 1005 S S

H

H Compound 1006 S S

H

H Compound 1007 S S

H

H Compound 1008 S S

H

H Compound 1009 S S

H

H Compound 1010 S S

H

H Compound 1011 S S

H

H Compound 1012 S S

H

H Compound 1013 S S

H

H Compound 1014 S S

H

H Compound 1015 S S

H

H Compound 1016 S S

H

H

TABLE 40 X^(b1) X^(b2) R^(b11) R^(b12) R^(b21) R^(b22) Compound 1017 S S

H

H Compound 1018 S S

H

H Compound 1019 S S

H

H Compound 1020 S S

H

H Compound 1021 S S

H

H Compound 1022 S S

H

H Compound 1023 S S

H

H Compound 1024 S S

H

H Compound 1025 S S

H

H Compound 1026 S S

H

H Compound 1027 S S

H

H Compound 1028 S S

H

H Compound 1029 S S

H

H Compound 1030 S S

H

H Compound 1031 S S

H

H Compound 1032 S S

H

H Compound 1033 S S

H

H Compound 1034 O O C₅H₁₁—* H C₅H₁₁—* H Compound 1035 O O C₆H₁₃—* HC₆H₁₃—* H Compound 1036 O O C₇H₁₅—* H C₇H₁₅—* H Compound 1037 O OC₈H₁₇—* H C₈H₁₇—* H Compound 1038 O O C₉H₁₉—* H C₉H₁₉—* H

TABLE 41 X^(b1) X^(b2) R^(b11) R^(b12) R^(b21) R^(b22) Compound 1039 O OC₁₀H₂₁—* H C₁₀H₂₁—* H Compound 1040 O O C₁₁H₂₃—* H C₁₁H₂₃—* H Compound1041 O O C₁₂H₂₅—* H C₁₂H₂₅—* H Compound 1042 O O C₁₃H₂₇—* H C₁₃H₂₇—* HCompound 1043 O O C₁₄H₂₉—* H C₁₄H₂₉—* H Compound 1044 O O C₁₅H₃₁—* HC₁₅H₃₁—* H Compound 1045 O O C₁₆H₃₃—* H C₁₆H₃₃—* H Compound 1046 O OC₁₇H₃₅—* H C₁₇H₃₅—* H Compound 1047 O O C₁₈H₃₇—* H C₁₈H₃₇—* H Compound1048 O O p-C₅H₁₁—Ph—* H p-C₅H₁₁—Ph—* H Compound 1049 O O p-C₆H₁₃—Ph—* Hp-C₆H₁₃—Ph—* H Compound 1050 O O p-C₇H₁₅—Ph—* H p-C₇H₁₅—Ph—* H Compound1051 O O p-C₈H₁₇—Ph—* H p-C₈H₁₇—Ph—* H Compound 1052 O O p-C₉H₁₉—Ph—* Hp-C₉H₁₉—Ph—* H Compound 1053 O O p-C₁₀H₂₁—Ph—* H p-C₁₀H₂₁—Ph—* HCompound 1054 O O p-C₁₁H₂₃—Ph—* H p-C₁₁H₂₃—Ph—* H Compound 1055 O Op-C₁₂H₂₅—Ph—* H p-C₁₂H₂₅—Ph—* H Compound 1056 O O p-C₁₃H₂₇—Ph—* Hp-C₁₃H₂₇—Ph—* H Compound 1057 O O p-C₁₄H₂₉—Ph—* H p-C₁₄H₂₉—Ph—* HCompound 1058 O O p-C₁₅H₃₁—Ph—* H p-C₁₅H₃₁—Ph—* H Compound 1059 O Op-C₁₆H₃₃—Ph—* H p-C₁₆H₃₃—Ph—* H Compound 1060 O O p-C₁₇H₃₅—Ph—* Hp-C₁₇H₃₅—Ph—* H Compound 1061 O O p-C₁₈H₃₇—Ph—* H p-C₁₈H₃₇—Ph—* HCompound 1062 O O

H

H Compound 1063 O O

H

H Compound 1064 O O

H

H Compound 1065 O O

H

H Compound 1066 O O

H

H Compound 1067 O O

H

H Compound 1068 O O

H

H Compound 1069 O O

H

H Compound 1070 O O

H

H Compound 1071 O O

H

H

TABLE 42 X^(b1) X^(b2) R^(b11) R^(b12) R^(b21) R^(b22) Compound 1072 O O

H

H Compound 1073 O O

H

H Compound 1074 O O

H

H Compound 1075 O O

H

H Compound 1076 S S C₄H₃OC₄H₈—* H C₄H₃OC₄H₈—* H Compound 1077 S SC₂H₅OC₂H₄—* H C₂H₅OC₂H₄—* H Compound 1078 S S C₆H₁₃OC₄H₈—* HC₆H₁₃OC₄H₈—* H Compound 1079 S S C₂H₅OC₄H₈—* H C₂H₅OC₄H₈—* H Compound1080 S S CH₃OC₃H₅—* H CH₃OC₃H₅—* H Compound 1081 S S

H

H Compound 1082 S S

H

H Compound 1083 S S

H

H Compound 1084 S S PhO₃H₆—* H PhO₃H₆—* H Compound 1085 S S PhOC₃H₆—* HPhOC₃H₆—* H Compound 1086 S S

H

H Compound 1087 S S

H

H Compound 1088 S S

H

H Compound 1089 S S

H

H Compound 1090 S S

H

H Compound 1091 S S 3,7-Dimethyloctyl H 3,7-Dimethyloctyl H Compound1092 S S 3,7-Dimethyloctyl H H H Compound 1093 S S 2-Ethylhexyl H2-Ethylhexyl H Compound 1094 S S

H

H Compound 1095 S S

H

H

TABLE 43 X^(b1) X^(b2) R^(b11) R^(b12) R^(b21) R^(b22) Compound 1096 S S

H

H Compound 1097 S S

H H H Compound 1098 S S

H

H Compound 1099 S S C₅H₁₁—* H

H Compound 1100 S S

H

H Compound 1101 S S

H

H Compound 1102 S S

H

H Compound 1103 S S

H

H Compound 1104 S S

H

H Compound 1105 S S

H H H Compound 1106 S S

H

H Compound 1107 S S

H

H Compound 1108 S S

H

H Compound 1109 S S

H

H

TABLE 44 X^(c1) X^(c2) R^(c11) R^(c21) Compound S S C₅H₁₁—* C₅H₁₁—* 1110Compound S S C₆H₁₃—* C₆H₁₃—* 1111 Compound S S C₇H₁₅—* C₇H₁₅—* 1112Compound S S C₈H₁₇—* C₈H₁₇—* 1113 Compound S S C₉H₁₉—* C₉H₁₉—* 1114Compound S S C₁₀H₂₁—* C₁₀H₂₁—* 1115 Compound S S C₁₁H₂₃—* C₁₁H₂₃—* 1116Compound S S C₁₂H₂₅—* C₁₂H₂₅—* 1117 Compound S S C₁₃H₂₇—* C₁₃H₂₇—* 1118Compound S S C₁₄H₂₉—* C₁₄H₂₉—* 1119 Compound S S C₁₅H₃₁—* C₁₅H₃₁—* 1120Compound S S C₁₆H₃₃—* C₁₆H₃₃—* 1121 Compound S S C₁₇H₃₅—* C₁₇H₃₅—* 1122Compound S S C₁₈H₃₇—* C₁₈H₃₇—* 1123 Compound S S p-C₅H₁₁—Ph—*p-C₅H₁₁—Ph—* 1124 Compound S S p-C₆H₁₃—Ph—* p-C₆H₁₃—Ph—* 1125 Compound SS p-C₇H₁₅—Ph—* p-C₇H₁₅—Ph—* 1126 Compound S S p-C₈H₁₇—Ph—* p-C₈H₁₇—Ph—*1127 Compound S S p-C₉H₁₉—Ph—* p-C₉H₁₉—Ph—* 1128 Compound S Sp-C₁₀H₂₁—Ph—* p-C₁₀H₂₁—Ph—* 1129 Compound S S p-C₁₁H₂₃—Ph—*p-C₁₁H₂₃—Ph—* 1130 Compound S S p-C₁₂H₂₅—Ph—* p-C₁₂H₂₅—Ph—* 1131Compound S S p-C₁₃H₂₇—Ph—* p-C₁₃H₂₇—Ph—* 1132 Compound S S p-C₁₄H₂₉—Ph—*p-C₁₄H₂₉—Ph—* 1133 Compound S S p-C₁₅H₃₁—Ph—* p-C₁₅H₃₁—Ph—* 1134Compound S S p-C₁₆H₃₃—Ph—* p-C₁₆H₃₃—Ph—* 1135 Compound S S p-C₁₇H₃₅—Ph—*p-C₁₇H₃₅—Ph—* 1136 Compound S S p-C₁₈H₃₇—Ph—* p-C₁₈H₃₇—Ph—* 1137Compound 1138 S S

Compound 1139 S S

Compound 1140 S S

Compound 1141 S S

Compound 1142 S S

Compound 1143 S S

Compound 1144 S S

Compound 1145 S S

TABLE 45 x^(c1) X^(c2) R^(c11) R^(c21) Com- pound 1146 S S

Com- pound 1147 S S

Com- pound 1148 S S

Com- pound 1149 S S

Com- pound 1150 S S

Com- pound 1151 S S

Com- pound 1152 S S

Com- pound 1153 S S

Com- pound 1154 S S

Com- pound 1155 S S

Com- pound 1156 S S

Com- pound 1157 S S

Com- pound 1158 S S

Com- pound 1159 S S

Com- pound 1160 S S

Com- pound 1161 S S

Com- pound 1162 S S

Com- pound 1163 S S

TABLE 46 X^(c1) X^(c2) R^(c11) R^(c21) Com- pound 1164 S S

Com- pound 1165 S S

Com- S S H C₅H₁₁—* pound 1166 Com- S S H C₆H₁₃—* pound 1167 Com- S S HC₇H₁₅—* pound 1168 Com- S S H C₈H₁₇—* pound 1169 Com- S S H C₉H₁₉—*pound 1170 Com- S S H C₁₀H₂₁—* pound 1171 Com- S S H C₁₁H₂₃—* pound 1172Com- S S H C₁₂H₂₅—* pound 1173 Com- S S H C₁₃H₂₇—* pound 1174 Com- S S HC₁₄H₂₉—* pound 1175 Com- S S H C₁₅H₃₁—* pound 1176 Com- S S H C₁₆H₃₃—*pound 1177 Com- S S H C₁₇H₃₅—* pound 1178 Com- S S H C₁₈H₃₇—* pound 1179Com- S S Ph C₅H₁₁—* pound 1180 Com- S S Ph C₆H₁₃—* pound 1181 Com- S SPh C₇H₁₅—* pound 1182 Com- S S Ph C₈H₁₇—* pound 1183 Com- S S Ph C₉H₁₉—*pound 1184 Com- S S Ph C₁₀H₂₁—* pound 1185 Com- S S Ph C₁₁H₂₃—* pound1186 Com- S S Ph C₁₂H₂₅—* pound 1187 Com- S S Ph C₁₃H₂₇—* pound 1188Com- S S Ph C₁₄H₂₉—* pound 1189 Com- S S Ph C₁₅H₃₁—* pound 1190 Com- S SPh C₁₆H₃₃—* pound 1191 Com- S S Ph C₁₇H₃₅—* pound 1192 Com- S S PhC₁₈H₃₇—* pound 1193 Com- pound 1194 S S

C₅H₁₁—* Com- pound 1195 S S

C₆H₁₃—* Com- pound 1196 S S

C₇H₁₅—* Com- pound 1197 S S

C₈H₁₇—* Com- pound 1198 S S

C₉H₁₉—* Com- pound 1199 S S

C₁₀C₂₁—*

TABLE 47 X^(c1) X^(c2) R^(c11) R^(c21) Compound 1200 S S

C₁₁C₂₃—* Compound 1201 S S

C₁₂C₂₅—* Compound 1202 S S

C₁₃C₂₇—* Compound 1203 S S

C₁₄C₂₉—* Compound 1204 S S

C₁₅C₃₁—* Compound 1205 S S

C₁₆C₃₃—* Compound 1206 S S

C₁₇C₃₅—* Compound 1207 S S

C₁₈C₃₇—* Compound 1208 S S H p-C₅H₁₁—Ph—* Compound 1209 S S Hp-C₆H₁₃—Ph—* Compound 1210 S S H p-C₇H₁₅—Ph—* Compound 1211 S S Hp-C₈H₁₇—Ph—* Compound 1212 S S H p-C₉H₁₉—Ph—* Compound 1213 S S Hp-C₁₀H₂₁—Ph—* Compound 1214 S S H p-C₁₁H₂₃—Ph—* Compound 1215 S S Hp-C₁₂H₂₅—Ph—* Compound 1216 S S H p-C₁₃H₂₇—Ph—* Compound 1217 S S Hp-C₁₄H₂₉—Ph—* Compound 1218 S S H p-C₁₅H₃₁—Ph—* Compound 1219 S S Hp-C₁₆H₃₃—Ph—* Compound 1220 S S H p-C₁₇H₃₅—Ph—* Compound 1221 S S Hp-C₁₈H₃₇—Ph—* Compound 1222 S S Ph p-C₅H₁₁—Ph—* Compound 1223 S S Php-C₆H₁₃—Ph—* Compound 1224 S S Ph p-C₇H₁₅—Ph—* Compound 1225 S S Php-C₈H₁₇—Ph—* Compound 1226 S S Ph p-C₉H₁₉—Ph—* Compound 1227 S S Php-C₁₀H₂₁—Ph—* Compound 1228 S S Ph p-C₁₁H₂₃—Ph—* Compound 1229 S S Php-C₁₂H₂₅—Ph—* Compound 1230 S S Ph p-C₁₃H₂₇—Ph—* Compound 1231 S S Php-C₁₄H₂₉—Ph—* Compound 1232 S S Ph p-C₁₅H₃₁—Ph—* Compound 1233 S S Php-C₁₆H₃₃—Ph—* Compound 1234 S S Ph p-C₁₇H₃₅—Ph—* Compound 1235 S S Php-C₁₈H₃₇—Ph—*

TABLE 48 X^(c1) X^(c2) R^(c11) R^(c21) Compound 1236 S S

p-C₅H₁₁—Ph—* Compound 1237 S S

p-C₆H₁₃—Ph—* Compound 1238 S S

p-C₇H₁₅—Ph—* Compound 1239 S S

p-C₈H₁₇—Ph—* Compound 1240 S S

p-C₉H₁₉—Ph—* Compound 1241 S S

p-C₁₀H₂₁—Ph—* Compound 1242 S S

p-C₁₁H₂₃—Ph—* Compound 1243 S S

p-C₁₂H₂₅—Ph—* Compound 1244 S S

p-C₁₃H₂₇—Ph—* Compound 1245 S S

p-C₁₄H₂₉—Ph—* Compound 1246 S S

p-C₁₅H₃₁—Ph—* Compound 1247 S S

p-C₁₆H₃₃—Ph—* Compound 1248 S S

p-C₁₇H₃₅—Ph—* Compound 1249 S S

p-C₁₈H₃₇—Ph—* Compound 1250 S S H

Compound 1251 S S H

Compound 1252 S S H

Compound 1253 S S H

TABLE 49 X^(c1) X^(c2) R^(c11) R^(c21) Compound 1254 S S H

Compound 1255 S S H

Compound 1256 S S H

Compound 1257 S S H

Compound 1258 S S H

Compound 1259 S S H

Compound 1260 S S H

Compound 1261 S S H

Compound 1262 S S H

Compound 1263 S S Ph

Compound 1264 S S Ph

Compound 1265 S S Ph

Compound 1266 S S Ph

Compound 1267 S S Ph

Compound 1268 S S Ph

Compound 1269 S S Ph

Compound 1270 S S Ph

Compound 1271 S S Ph

TABLE 50 X^(c1) X^(c2) R^(c11) R^(c21) Com- pound 1272 S S Ph

Com- pound 1273 S S Ph

Com- pound 1274 S S Ph

Com- pound 1275 S S Ph

Com- pound 1276 S S

Com- pound 1277 S S

Com- pound 1278 S S

Com- pound 1279 S S

Com- pound 1280 S S

Com- pound 1281 S S

Com- pound 1282 S S

Com- pound 1283 S S

Com- pound 1284 S S

Com- pound 1285 S S

Com- pound 1286 S S

Com- pound 1287 S S

Com- pound 1288 S S

Com- pound 1289 S S H

TABLE 51 X^(c1) X^(c2) R^(c11) R^(c21) Compound 1290 S S H

Compound 1291 S S H

Compound 1292 S S H

Compound 1293 S S H

Compound 1294 S S H

Compound 1295 S S H

Compound 1296 S S H

Compound 1297 S S H

Compound 1298 S S H

Compound 1299 S S H

Compound 1300 S S H

Compound 1301 S S H

Compound 1302 S S H

Compound 1303 S S Ph

Compound 1304 S S Ph

Compound 1305 S S Ph

Compound 1306 S S Ph

Compound 1307 S S Ph

TABLE 52 X^(c1) X^(c2) R^(c11) R^(c21) Compound 1308 S S Ph

Compound 1309 S S Ph

Compound 1310 S S Ph

Compound 1311 S S Ph

Compound 1312 S S Ph

Compound 1313 S S Ph

Compound 1314 S S Ph

Compound 1315 S S Ph

Compound 1316 S S Ph

Compound 1317 S S

Compound 1318 S S

Compound 1319 S S

Compound 1320 S S

Compound 1321 S S

Compound 1322 S S

Compound 1323 S S

Compound 1324 S S

Compound 1325 S S

TABLE 53 X^(c1) X^(c2) R^(c11) R^(c21) Com- pound 1326 S S

Com- pound 1327 S S

Com- pound 1328 S S

Com- pound 1329 S S

Com- pound 1330 S S

Com- S S C₁₀H₂₁—* p-C₅H₁₁—Ph—* pound 1331 Com- S S C₁₀H₂₁—* p-C₆H₁₃—Ph—*pound 1332 Com- S S C₁₀H₂₁—* p-C₇H₁₅—Ph—* pound 1333 Com- S S C₁₀H₂₁—*p-C₈H₁₇—Ph—* pound 1334 Com- S S C₁₀H₂₁—* p-C₉H₁₉—Ph—* pound 1335 Com- SS C₁₀H₂₁—* p-C₁₀H₂₁—Ph—* pound 1336 Com- S S C₁₀H₂₁—* p-C₁₁H₂₃—Ph—*pound 1337 Com- S S C₁₀H₂₁—* p-C₁₂H₂₅—Ph—* pound 1338 Com- S S C₁₀H₂₁—*p-C₁₃H₂₇—Ph—* pound 1339 Com- S S C₁₀H₂₁—* p-C₁₄H₂₉—Ph—* pound 1340 Com-S S C₁₀H₂₁—* p-C₁₅H₃₁—Ph—* pound 1341 Com- S S C₁₀H₂₁—* p-C₁₆H₃₃—Ph—*pound 1342 Com- S S C₁₀H₂₁—* p-C₁₇H₃₅—Ph—* pound 1343 Com- S S C₁₀H₂₁—*p-C₁₈H₃₇—Ph—* pound 1344 Com- pound 1345 S S C₁₂H₂₅—*

Com- pound 1346 S S C₁₂H₂₅—*

Com- pound 1347 S S C₁₂H₂₅—*

Com- pound 1348 S S C₁₂H₂₅—*

Com- pound 1349 S S C₁₂H₂₅—*

Com- pound 1350 S S C₁₂H₂₅—*

Com- pound 1351 S S C₁₂H₂₅—*

Com- pound 1352 S S C₁₂H₂₅—*

TABLE 54 X^(c1) X^(c2) R^(c11) R^(c21) Compound 1353 S S C₁₂H₂₅—*

Compound 1354 S S C₁₂H₂₅—*

Compound 1355 S S C₁₂H₂₅—*

Compound 1356 S S C₁₂H₂₅—*

Compound 1357 S S C₁₂H₂₅—*

Compound 1358 S S C₁₂H₂₅—*

Compound 1359 S S

Compound 1360 S S

Compound 1361 S S

Compound 1362 S S

Compound 1363 S S

Compound 1364 S S

Compound 1365 S S

Compound 1366 S S

Compound 1367 S S

Compound 1368 S S

Compound 1369 S S

Compound 1370 S S

TABLE 55 X^(c1) X^(c2) R^(c11) R^(c21) Compound 1371 S S

Compound 1372 S S

Compound 1373 S S

Compound 1374 S S

Compound 1375 S S

Compound 1376 S S

Compound 1377 S S

Compound 1378 S S

Compound 1379 S S

Compound 1380 S S

Compound 1381 S S

Compound 1382 S S

Compound 1383 S S

Compound 1384 S S

Compound 1385 S S

Compound 1386 S S

Compound 1387 S S

Compound 1388 S S

TABLE 56 X^(c1) X^(c2) X^(c11) X^(c21) Compound 1389 S S

Compound 1390 S S

Compound 1391 S S

Compound 1392 S S

Compound 1393 S S

Compound 1394 S S

Compound 1395 S S

Compound 1396 S S

Compound 1397 S S

Compound 1398 S S

Compound 1399 S S

Compound 1400 O O C₅H₁₁—* C₅H₁₁—* Compound 1401 O O C₆H₁₃—* C₆H₁₃—*Compound 1402 O O C₇H₁₅—* C₇H₁₅—* Compound 1403 O O C₈H₁₇—* C₈H₁₇—*Compound 1404 O O C₉H₁₉—* C₉H₁₉—* Compound 1405 O O C₁₀H₂₁—* C₁₀H₂₁—*Compound 1406 O O C₁₁H₂₃—* C₁₁H₂₃—* Compound 1407 O O C₁₂H₂₅—* C₁₂H₂₅—*Compound 1408 O O C₁₃H₂₇—* C₁₃H₂₇—* Compound 1409 O O C₁₄H₂₉—* C₁₄H₂₉—*Compound 1410 O O C₁₅H₃₁—* C₁₅H₃₁—* Compound 1411 O O C₁₆H₃₃—* C₁₆H₃₃—*Compound 1412 O O C₁₇H₃₅—* C₁₇H₃₅—* Compound 1413 O O C₁₈H₃₇—* C₁₈H₃₇—*Compound 1414 O O p-C₅H₁₁—Ph—* p-C₅H₁₁—Ph—* Compound 1415 O Op-C₆H₁₃—Ph—* p-C₆H₁₃—Ph—* Compound 1416 O O p-C₇H₁₅—Ph—* p-C₇H₁₅—Ph—*Compound 1417 O O p-C₈H₁₇—Ph—* p-C₈H₁₇—Ph—* Compound 1418 O Op-C₉H₁₉—Ph—* p-C₉H₁₉—Ph—* Compound 1419 O O p-C₁₀H₂₁—Ph—* p-C₁₀H₂₁—Ph—*Compound 1420 O O p-C₁₁H₂₃—Ph—* p-C₁₁H₂₃—Ph—* Compound 1421 O Op-C₁₂H₂₅—Ph—* p-C₁₂H₂₅—Ph—*

TABLE 57 X^(c1) X^(c2) R^(c11) R^(c21) Com- O O p-C₁₃H₂₇—Ph—*p-C₁₃H₂₇—Ph—* pound 1422 Com- O O p-C₁₄H₂₉—Ph—* p-C₁₄H₂₉—Ph—* pound 1423Com- O O p-C₁₅H₃₁—Ph—* p-C₁₅H₃₁—Ph—* pound 1424 Com- O O p-C₁₆H₃₃—Ph—*p-C₁₆H₃₃—Ph—* pound 1425 Com- O O p-C₁₇H₃₅—Ph—* p-C₁₇H₃₅—Ph—* pound 1426Com- O O p-C₁₈H₃₇—Ph—* p-C₁₈H₃₇—Ph—* pound 1427 Com- pound 1428 O O

Com- pound 1429 O O

Com- pound 1430 O O

Com- pound 1431 O O

Com- pound 1432 O O

Com- pound 1433 O O

Com- pound 1434 O O

Com- pound 1435 O O

Com- pound 1436 O O

Com- pound 1437 O O

Com- pound 1438 O O

Com- pound 1439 O O

Com- pound 1440 O O

Com- pound 1441 O O

Com- S S C₄H₃OC₄H₈—* C₄H₃OC₄H₈—* pound 1442 Com- S S C₂H₅OC₂H₄—*C₂H₅OC₂H₄—* pound 1443

TABLE 58 X^(c1) X^(c2) R^(c11) R^(c12) Compound 1444 S S C₆H₁₃OC₄H₈—*C₆H₁₃OC₄H₈—* Compound 1445 S S C₂H₅OC₄H₈—* C₂H₅OC₄H₈—* Compound 1446 S SCH₃OC₃H₆—* CH₃OC₃H₆—* Compound 1447 S S

Compound 1448 S S

Compound 1449 S S

Compound 1450 S S PhC₃H₆—* PhC₃H₆—* Compound 1451 S S PhOC₃H₆—*PhOC₃H₆—* Compound 1452 S S

Compound 1453 S S

Compound 1454 S S

Compound 1455 S S

Compound 1456 S S

Compound 1457 S S 3,7-Dimethyloctyl 3,7-Dimethyloctyl Compound 1458 S S3,7-Dimethyloctyl H Compound 1459 S S 2-Ethylhexyl 2-Ethylhexyl Compound1460 S S

Compound 1461 S S

TABLE 59 X^(c1) X^(c2) R^(c11) R^(c21) Compound 1462 S S

Compound 1463 S S

H Compound 1464 S S

Compound 1465 S S C₅H₁₁—*

Compound 1466 S S

Compound 1467 S S

Compound 1468 S S

Compound 1469 S S

Compound 1470 S S

Compound 1471 S S

H Compound 1472 S S

Compound 1473 S S

Compound 1474 S S

Compound 1475 S S

In the organic semiconductor layer of the organic semiconductor elementaccording to the present invention or the organic semiconductor filmaccording to the present invention described below, the content of thespecific compound is preferably 30 to 100 mass %, more preferably 50 to100 mass %, and even more preferably 70 to 100 mass %. In a case where abinder polymer described below is not contained, the content ispreferably 90 to 100 mass % and more preferably 95 to 100 mass %.

<Binder Polymer>

The organic semiconductor layer of the organic semiconductor elementaccording to the present invention preferably contains the binderpolymer.

The organic semiconductor element according to the present invention maybe an organic semiconductor element having a layer including the organicsemiconductor layer and the binder polymer.

The types of the binder polymer are not particularly limited, andwell-known binder polymers can be used.

Examples of the binder polymer include a polystyrene resin, an acrylicresin, rubber, and a thermoplastic elastomer.

Among these, as the binder polymer, a polymer compound (a polymer havinga monomer unit having a benzene ring group) having a benzene ring ispreferable. The content of the monomer unit having a benzene ring groupis not particularly limited. However, the content is preferably 50 mol %or greater, more preferably 70 mol % or greater, and even morepreferably 90 mol % or greater with respect to the entire monomer unit.The upper limit is not particularly limited, but examples of the upperlimit include 100 mol %.

Examples of the binder polymer include polystyrene,poly(α-methylstyrene), polyvinyl cinnamate, poly(4-vinylphenyl), andpoly(4-methylstyrene).

A weight-average molecular weight of the binder polymer is notparticularly limited, but is preferably 1,000 to 2,000,000, morepreferably 3,000 to 1,000,000, and even more preferably 5,000 to600,000.

In a case where a solvent described below is used, it is preferable thatthe binder polymer exhibits solubility higher than the solubility of thespecific compound in a used solvent. If the above aspect is adopted,mobility and heat stability of the obtained organic semiconductor arefurther improved.

A content of the binder polymer in the organic semiconductor layer ofthe organic semiconductor element of the present invention is preferably1 to 200 parts by mass, more preferably 10 to 150 parts by mass, andeven more preferably 20 to 120 parts by mass with respect to 100 partsby mass of the content of the specific compound. If the content iswithin the above range, mobility and heat stability of the obtainedorganic semiconductor are further improved.

<Other Components>

Other components may be included other than the specific compound andthe binder polymer may be included in the organic semiconductor layeraccording to the organic semiconductor element of the present invention.

As other components, known additives and the like can be used.

In the organic semiconductor layer, a content of the components otherthan the specific compound and the binder polymer is preferably 10 mass% or less, more preferably 5 mass % or less, even more preferably 1 mass% or less, and particularly preferably 0.1 mass % or less. If thecontent of other components is within the above range, film formabilityis improved, and mobility and heat stability of the obtained organicsemiconductor are further improved.

(Method of Forming Organic Semiconductor Layer)

The method of forming the organic semiconductor layer according to theorganic semiconductor element of the present invention is notparticularly limited. However, a desired organic semiconductor layer canbe formed by applying the composition for forming the organicsemiconductor film according to the present invention described below toa source electrode, a drain electrode, and a gate insulating film andperforming a drying treatment, if necessary.

(Method of Manufacturing Organic Semiconductor Element and OrganicSemiconductor Film)

The organic semiconductor element and an organic semiconductor film ofthe present invention is preferably manufactured using the compositionfor forming an organic semiconductor film of the present inventiondescribed below.

A method of manufacturing an organic semiconductor film or an organicsemiconductor element by using the composition for forming an organicsemiconductor film of the present invention is not particularly limited,and known methods can be adopted. Examples thereof include a method ofmanufacturing an organic semiconductor film by applying the compositiononto a predetermined base material and if necessary, performing a dryingtreatment.

The method of applying the composition onto a base material is notparticularly limited, and known methods can be adopted. Examples thereofinclude an ink jet printing method, a flexographic printing method, abar coating method, a spin coating method, a knife coating method, adoctor blade method, and the like. Among these, an ink jet printingmethod and a flexographic printing method are preferable.

Preferred examples of the flexographic printing method include an aspectin which a photosensitive resin plate is used as a flexographic printingplate. By printing the composition onto a substrate according to theaspect, a pattern can be easily formed.

Among these, the method of manufacturing an organic semiconductorelement and an organic semiconductor film according to the presentinvention preferably include an applying step of applying an compositionfor forming an organic semiconductor film according to the presentinvention to a substrate and a removing step of removing at least aportion of a solvent having a boiling point of 100° C. or higherincluded in the composition for forming the organic semiconductor film.

<Solvent Having Boiling Point of 100° C. or Higher>

The composition for forming the organic semiconductor film according tothe present invention contains a solvent having a boiling point of 100°C. or higher (hereinafter, referred to a “specific solvent”).

Examples of the specific solvent include a hydrocarbon-based solventsuch as octane, decane, toluene, xylene, mesitylene, ethylbenzene,decalin, 1-methylnaphthalene, tetralin, and dimethyltetralin, aketone-based solvent such as methyl isobutyl ketone and cyclohexanone, ahalogenated hydrocarbon-based solvent such as tetrachloroethane,chlorobenzene, dichlorobenzene, chlorotoluene, 1-fluoronaphthalene, and1-chloronaphthalene, an ester-based solvent such as butyl acetate andamyl acetate, an alcohol-based solvent such as butanol, pentanol,hexanol, cyclohexanol, methyl cellosolve, ethyl cellosolve, and ethyleneglycol, an ether-based solvent such as dibutyl ether, dioxane, anisole,4-tertiary butyl anisole, and m-dimethoxybenzene, an amide-based solventsuch as N,N-dimethylformamide and N,N-dimethylacetamide, an imide-basedsolvent such as 1-methyl-2-pyrrolidone and 1-methyl-2-imidazolidinone, asulfoxide-based solvent such as dimethyl sulfoxide, and a nitrile-basedsolvent such as butyronitrile and benzonitrile.

The specific solvent may be used singly or two or more types thereof maybe used in combination.

Among these, a hydrocarbon-based solvent, a halogenatedhydrocarbon-based solvent and/or an ether-based solvent are preferable,toluene, xylene, mesitylene, tetralin, dichlorobenzene, or anisole ismore preferable, and toluene is even more preferable.

If the specific solvent is the aforementioned solvent, coatingproperties are excellent, and thus an organic semiconductor film can beeasily formed.

In view of stability of the composition for forming the organicsemiconductor film, forming an even film, and drying, the boiling pointof the specific solvent in normal pressure is 100° C. or higher,preferably 100° C. to 300° C., more preferably 100° C. to 200° C., andeven more preferably 100° C. to 150° C.

The drying treatment in the removing step is a treatment performed ifnecessary, and the optimal treatment conditions are suitably selectedaccording to the type of the specific compound used and the solvent. Inview of further improving mobility and heat stability of the obtainedorganic semiconductor and improving productivity, a heating temperatureis preferably 30° C. to 100° C. and more preferably 40° C. to 80° C.,and a heating time is preferably 10 to 300 minutes and more preferably30 to 180 minutes.

A thickness of the formed organic semiconductor layer is notparticularly limited. From the viewpoint of mobility and heat stabilityof the obtained organic semiconductor, the film thickness is preferably10 to 500 nm and more preferably 30 to 200 nm.

<Organic Semiconductor Element>

The organic semiconductor element is not particularly limited, but ispreferably an organic semiconductor element having 2 to 5 terminals, andmore preferably an organic semiconductor element having 2 or 3terminals.

It is preferable that the organic semiconductor element is not aphotoelectric conversion element.

The organic semiconductor element according to the present invention ispreferably a non-luminous organic semiconductor element.

Examples of a 2-terminal element include a rectifier diode, a constantvoltage diode, a PIN diode, a Schottky barrier diode, a surge protectiondiode, a diac, a varistor, a tunnel diode, and the like.

Examples of a 3-terminal element include a bipolar transistor, aDarlington transistor, a field effect transistor, insulated gate bipolartransistor, a uni-junction transistor, a static induction transistor, agate turn-off thyristor, a triac, a static induction thyristor, and thelike.

Among these, a rectifier diode and transistors are preferable, and afield effect transistor is more preferable.

An aspect of the organic thin film transistor of the present inventionwill be described with reference to drawings.

FIG. 1 is a schematic cross-sectional view of an aspect of an organicsemiconductor element (organic thin film transistor (organic TFT)) ofthe present invention.

In FIG. 1, an organic thin film transistor 100 includes a substrate 10,a gate electrode 20 disposed on the substrate 10, a gate insulating film30 covering the gate electrode 20, a source electrode 40 and a drainelectrode 42 which contact a surface of the gate insulating film 30 thatis on the side opposite to the gate electrode 20 side, an organicsemiconductor film 50 covering a surface of the gate insulating film 30between the source electrode 40 and the drain electrode 42, and asealing layer 60 covering each member. The organic thin film transistor100 is a bottom gate-bottom contact type organic thin film transistor.

In FIG. 1, the organic semiconductor film 50 corresponds to a filmformed of the composition described above.

Hereinafter, the substrate, the gate electrode, the gate insulatingfilm, the source electrode, the drain electrode, the organicsemiconductor film, the sealing layer, and methods for forming each ofthese will be specifically described.

<Substrate>

The substrate plays a role of supporting the gate electrode, the sourceelectrode, the drain electrode, and the like which will be describedlater.

The type of the substrate is not particularly limited, and examplesthereof include a plastic substrate, a glass substrate, a ceramicsubstrate, and the like. Among these, from the viewpoint ofapplicability to each device and costs, a glass substrate or a plasticsubstrate is preferable.

Examples of materials of the plastic substrate include a thermosettingresin (for example, an epoxy resin, a phenol resin, a polyimide resin,or a polyester resin (for example, polyethylene terephthalate (PET) orpolyethylene naphthalate (PEN)) and a thermoplastic resin (for example,a phenoxy resin, a polyethersulfone, polysulfone, or polyphenylenesulfone).

Examples of materials of the ceramic substrate include alumina, aluminumnitride, zirconia, silicon, silicon nitride, silicon carbide, and thelike.

Examples of materials of the glass substrate include soda lime glass,potash glass, borosilicate glass, quartz glass, aluminosilicate glass,lead glass, and the like.

<Gate Electrode, Source Electrode, and Drain Electrode>

Examples of materials of the gate electrode, the source electrode, andthe drain electrode include a metal such as gold (Au), silver, aluminum(Al), copper, chromium, nickel, cobalt, titanium, platinum, tantalum,magnesium, calcium, barium, or sodium; a conductive oxide such as InO₂,SnO₂, or indium tin oxide (ITO); a conductive polymer such aspolyaniline, polypyrrole, polythiophene, polyacetylene, orpolydiacetylene; a semiconductor such as silicon, germanium, or galliumarsenide; a carbon material such as fullerene, carbon nanotubes, orgraphite; and the like. Among these, a metal is preferable, and silverand aluminum are more preferable.

A thickness of each of the gate electrode, the source electrode, and thedrain electrode is not particularly limited, but is preferably 20 to 200nm.

A method of forming the gate electrode, the source electrode, and thedrain electrode is not particularly limited, but examples thereofinclude a method of vacuum vapor-depositing or sputtering an electrodematerial onto a substrate, a method of coating a substrate with acomposition for forming an electrode, a method of printing a compositionfor forming an electrode onto a substrate, and the like. Furthermore, ina case where the electrode is patterned, examples of the patterningmethod include a photolithography method; a printing method such as inkjet printing, screen printing, offset printing, or relief printing; amask vapor deposition method; and the like.

<Gate Insulating Film>

Examples of materials of the gate insulating film include a polymer suchas polymethyl methacrylate, polystyrene, polyvinylphenol, polyimide,polycarbonate, polyester, polyvinylalcohol, polyvinyl acetate,polyurethane, polysulfone, polybenzoxazole, polysilsesquioxane, an epoxyresin, or a phenol resin; an oxide such as silicon dioxide, aluminumoxide, or titanium oxide; a nitride such as silicon nitride; and thelike. Among these materials, in view of the compatibility with theorganic semiconductor film, a polymer is preferable.

In a case where a polymer is used as the material of the gate insulatingfilm, it is preferable to use a cross-linking agent (for example,melamine) in combination. If the cross-linking agent is used incombination, the polymer is cross-linked, and durability of the formedgate insulating film is improved.

A film thickness of the gate insulating film is not particularlylimited, but is preferably 100 to 1,000 nm.

A method of forming the gate insulating film is not particularlylimited, but examples thereof include a method of coating a substrate,on which the gate electrode is formed, with a composition for forming agate insulating film, a method of vapor-depositing or sputtering thematerial of the gate insulating film onto a substrate on which the gateelectrode is formed, and the like. A method of coating theaforementioned substrate with the composition for forming a gateinsulating film is not particularly limited, and it is possible to use aknown method (a bar coating method, a spin coating method, a knifecoating method, or a doctor blade method).

In a case where the gate insulating film is formed by coating thesubstrate with the composition for forming a gate insulating film, forthe purpose of removing the solvent, causing cross-linking, or the like,the composition may be heated (baked) after coating.

<Organic Semiconductor Film>

The organic semiconductor film according to the present invention is afilm formed of the composition for forming the organic semiconductorfilm according to the present invention.

The method of forming the organic semiconductor film is not particularlylimited. A desired organic semiconductor film can be formed by applyingthe aforementioned composition to a source electrode, a drain electrode,and a gate insulating film and performing a drying treatment, ifdesired.

<Binder Polymer Layer>

The organic semiconductor element of the present invention preferablyhas a layer of the aforementioned binder polymer between theaforementioned organic semiconductor layer and an insulating film, andmore preferably has a layer of the aforementioned binder polymer betweenthe aforementioned organic semiconductor layer and the gate insulatingfilm. A film thickness of the binder polymer layer is not particularlylimited, but is preferably 20 to 500 nm. The binder polymer layer shouldbe a layer containing the aforementioned polymer, and is preferably alayer composed of the aforementioned binder polymer.

A method of forming the binder polymer layer is not particularlylimited, and a known method (a bar coating method, a spin coatingmethod, a knife coating method, a doctor blade method, or an ink jetmethod) can be used.

In a case where the binder polymer layer is formed by performing coatingby using a composition for forming a binder polymer layer, for thepurpose of removing a solvent, causing cross-linking, or the like, thecomposition may be heated (baked) after coating.

<Sealing Layer>

From the viewpoint of durability, the organic semiconductor element ofthe present invention preferably includes a sealing layer as anoutermost layer. In the sealing layer, a known sealant can be used.

A thickness of the sealing layer is not particularly limited, but ispreferably 0.2 to 10 μm.

A method of forming the sealing layer is not particularly limited, butexamples thereof include a method of coating a substrate, on which thegate electrode, the gate insulating film, the source electrode, thedrain electrode, and the organic semiconductor film are formed, with acomposition for forming a sealing layer, and the like. Specific examplesof the method of coating the substrate with the composition for forminga sealing layer are the same as the examples of the method of coatingthe substrate with the composition for forming a gate insulating film.In a case where the organic semiconductor film is formed by coating thesubstrate with the composition for forming a sealing layer, for thepurpose of removing the solvent, causing cross-linking, or the like, thecomposition may be heated (baked) after coating.

FIG. 2 is a schematic cross-sectional view of another aspect of theorganic semiconductor element (organic thin film transistor) of thepresent invention.

In FIG. 2, an organic thin film transistor 200 includes the substrate10, the gate electrode 20 disposed on the substrate 10, the gateinsulating film 30 covering the gate electrode 20, the organicsemiconductor film 50 disposed on the gate insulating film 30, thesource electrode 40 and the drain electrode 42 disposed on the organicsemiconductor film 50, and the sealing layer 60 covering each member.Herein, the source electrode 40 and the drain electrode 42 are formedusing the aforementioned composition of the present invention. Theorganic thin film transistor 200 is a top contact type organic thin filmtransistor.

The substrate, the gate electrode, the gate insulating film, the sourceelectrode, the drain electrode, the organic semiconductor film, and thesealing layer are as described above.

In FIGS. 1 and 2, the aspects of the bottom gate-bottom contact typeorganic thin film transistor and the bottom gate-top contact typeorganic thin film transistor were specifically described. However, theorganic semiconductor element of the present invention can also suitablyused in a top gate-bottom contact type organic thin film transistor anda top gate-top contact type organic thin film transistor.

The organic thin film transistor described above can be suitably usedfor electronic paper and a display device.

(Composition for Forming Organic Semiconductor Film)

The composition for forming the organic semiconductor film according tothe present invention contains a solvent having a boiling point of 100°C. or higher and a compound represented by Formula 1, and a content ofthe compound represented by Formula 1 is 20 mass % or less with respectto a total amount of the composition for forming the organicsemiconductor film.

The composition for forming the organic semiconductor film according tothe present invention preferably contains a binder polymer.

The specific compound, the binder polymer, and the solvent in thecomposition for forming the organic semiconductor film according to thepresent invention are the same as the aforementioned specific compound,the aforementioned binder polymer, and the aforementioned solvent, andpreferable aspects are also the same.

The content of the specific compound of the composition for forming theorganic semiconductor film according to the present invention is 20 mass% or less, preferably 0.001 to 15 mass %, and more preferably 0.01 to 10mass % with respect to the total amount of the composition for formingthe organic semiconductor film. In a case where two or more types ofspecific compounds are used in combination, the total content of thespecific compounds is preferably in the range described above. If thecontent of the specific compound is in the range described above, theorganic semiconductor element having high mobility and high drivingstability can be obtained, storage stability of the composition forforming the organic semiconductor film is also satisfactory.

The content of the specific compound is preferably 30 to 100 mass %,more preferably 50 to 100 mass %, and even more preferably 70 to 100mass % with respect to the total solid content of the composition forforming the organic semiconductor film. In a case where a binder polymerdescribed below is not contained, the total content is preferably 90 to100 mass % and more preferably 95 to 100 mass %. The solid content is anamount of the component except for the volatile component such as thesolvent.

The content of the binder polymer in the composition for forming theorganic semiconductor film according to the present invention ispreferably greater than 0 mass % and 20 mass % or less, more preferably0.01 to 15 mass %, and even more preferably 0.25 to 10 mass % withrespect to the total amount of the composition for forming the organicsemiconductor film. If the content is in the range described above,mobility and heat resistance of the obtained organic semiconductorbecome more excellent.

The composition for forming the organic semiconductor film according tothe present invention may include other component in addition to thespecific compound and the binder polymer.

As the component, well-known additives may be used.

The content of the component in addition to the specific compound andthe binder polymer in the composition for forming the organicsemiconductor film according to the present invention is preferably 10mass % or less, more preferably 5 mass % or less, even more preferably 1mass % or less, and particularly preferably 0.1 mass % or less withrespect to the total solid content. If the content is in the rangedescribed above, film formability is improved, and mobility and heatstability of the obtained organic semiconductor are further improved.

The viscosity of the composition for forming the organic semiconductorfilm according to the present invention is not particularly limited.However, in view of excellent coating properties, the viscosity ispreferably 3 to 100 mPa·s, more preferably 5 to 50 mPa·s, and even morepreferably 9 to 40 mPa·s. The viscosity according to the presentinvention refers to viscosity at 25° C.

As a method of measuring the viscosity, a measuring method in conformityof JIS Z8803 is preferable.

The method of manufacturing the composition for forming the organicsemiconductor film according to the present invention is notparticularly limited, and well-known methods can be applied. Forexample, a desired composition can be obtained by adding a specificamount of a specific compound in the solvent and applying an suitablestirring treatment. In a case where the binder polymer is used, thespecific compound and the binder polymer are simultaneously orsequentially added, so as to suitably manufacture the composition.

EXAMPLES

Hereinafter, the present invention will be more specifically describedbased on examples. The materials and the amount thereof used, theproportion of the materials, the content and procedure of treatments,and the like described in the following examples can be suitably changedwithin a scope that does not depart from the gist of the presentinvention. Accordingly, the scope of the present invention is notlimited to the following specific examples. Herein, unless otherwisespecified, “part” and “%” are based on mass.

Specific Compounds and Synthesis Examples

Structures of E-1 to E-10 used in the examples and C-1 to C-2 used inthe comparative examples are provided below.

<Synthesis of E-1>

An intermediate M1 was synthesized according to a scheme X1 below.

The intermediate M1 and octyl zinc chloride were fused by negishicoupling reaction, so as to synthesize a compound E-1.

<Synthesis of E-2 to E-10>

E-2 to E-10 were also synthesized in the same manner as in E-1, exceptfor changing an organic zinc compound fused with the intermediate M1 tosuitable compounds.

<Synthesis of C-1>

A compound C-1 was synthesized according to the method described inJP2010-177637A.

<Synthesis of C-2>

A compound C-2 was synthesized according to the method disclosed inWO2013/168048A.

Examples 1 to 10 and Comparative Examples 1 to 2

<Manufacturing of TFT Element>

The specific compound presented in Table 60 or a comparative compound (1mg) and toluene (1 mL) were mixed with each other and heated to 100° C.,and the composition for forming the organic semiconductor film wasobtained.

An organic semiconductor film was formed by casting this composition toa substrate for measuring FET characteristics which was heated to 90° C.under the nitrogen atmosphere, and an organic thin film transistorelement for measuring FET characteristics was obtained. As the substratefor measuring FET characteristics, a silicon substrate in a bottomgate-bottom contact structure including chromium/gold (gate width W=100mm, gate length L=100 μm) arranged in a comb-shape as source and drainelectrodes and SiO₂ (film thickness: 200 nm) as an insulating film wasused.

The obtained composition was applied to a substrate for measuring FETcharacteristics by flexographic printing. Specifically, a flexographicprintability test machine F1 (manufactured by IGT Testing Systems) wasused as a printing machine, and AFP DSH 1.70% (manufactured by AsahiKasei Corporation)/a solid image was used as a flexographic resinversion. After printing was performed in a pressure between a plate anda substrate of 60 N and a transportation speed of 0.4 m/second, dryingwas performed at 40° C. for two hours, so as to form an organicsemiconductor film, and an organic thin film transistor element (organicTFT element) for measuring FET characteristics was obtained.

As the substrate for measuring FET characteristics, a silicon substratein a bottom gate-bottom contact structure including chromium/gold (gatewidth W=100 mm, gate length L=100 μm) arranged in a comb-shape as sourceand drain electrodes and SiO₂ (film thickness: 200 nm) as an insulatingfilm was used.

The ink was applied to the substrate for measuring FET characteristicsby ink jet printing. Specifically, DPP2831 (manufactured by FUJIFILMGlobal Graphic Systems Co., Ltd.) was used as an inkjet device and 10 pLheads were used, so as to form a solid film with a jetting frequency of2 Hz and a pitch between dots of 20 μm. Thereafter, drying was performedfor one hour at 70° C., so as to form an organic semiconductor film, andthe organic TFT element for measuring FET characteristics was obtained.

In the examples and the comparative examples, evaluations of mobility,coating film formability, and heat resistance described below withrespect to the organic TFT element obtained by ink jet printing were thesame as those of the organic TFT element obtained by casting thecomposition.

<Carrier Mobility (Mobility)>

With respect to the FET characteristics of the organic thin filmtransistor elements of the respective examples and the respectivecomparative examples, carrier mobility was evaluated under normalpressure and the nitrogen atmosphere by employing a semiconductorparameter analyzer (manufactured by Agilent, 4156C) to which a semiautomatic prober (manufactured by Vector Semiconductor Co., Ltd.,AX-2000) was connected.

A voltage of −80 V was applied between source electrodes and drainelectrodes of the respective organic thin film transistor elements (FETelements), a gate voltage was changed in the range of 20 V to −100 V, anequation below presenting a drain current Id was used, so as tocalculate carrier mobility μ.Id=(w/2L)μCi(Vg−Vth)²

In the equation, L represents a gate length, W represents a gate width,Ci represents capacitance of the insulating layer per unit area, Vgrepresents a gate voltage, and Vth represents a threshold voltage. Thenumerical value of the carrier mobility is required to be practically0.01 or greater, preferably 0.1 or greater, and more preferably 0.3 orgreater.

The expression “no characteristics” in the tables presents the createdelement did not have TFT characteristics.

<Coating Film Formability>

The compound according to the present invention or the comparativecompound (5 mg) and toluene (1 mL) were mixed and heated to 100° C., soas to obtain a non-luminescent organic semiconductor solution. Thiscoating liquid was casted under nitrogen atmosphere to the entiresurface of the substrate which was heated to 90° C. and on whichchannels for 50 elements were formed, so as to form an organicsemiconductor thin film, and 50 organic thin film transistor elementsfor measuring FET characteristics were obtained. Evaluation standards ofthe coating film formability were set as below, and the evaluationresults were presented in Table 60.

[Evaluation standard] A: 45 or more elements out of the obtained 50elements were driven as organic thin film transistor element

B: Less than 45 elements out of the obtained 50 elements were driven asorganic thin film transistor element

<Heat Resistance>

After the manufactured respective organic thin film transistor elementswere heated for one hour at 130° C. in a nitrogen glove box, carriermobility μ was measured, so as to calculate a carrier mobilitymaintenance rate after heating by the equation below.Carrier mobility maintenance rate after heating (%)=Carrier mobility(after heating)/carrier mobility (initial value)×100

Obtained results were evaluated according to evaluation standards below.The evaluation results are presented in Table 60. The expression “N/A”in the table means that a heat resistance was not performed since acreated element did not have TFT characteristics.

[Evaluation Standard]

A: Carrier mobility maintenance rate after heating was 95% or greater

B: Carrier mobility maintenance rate after heating was 70% or greaterand less than 95%

C: Carrier mobility maintenance rate after heating was 40% or greaterand less than 70%

D: Carrier mobility maintenance rate after heating was 20% or greaterand less than 40%

E: Carrier mobility maintenance rate after heating was less than 20%

TABLE 60 Specific Solu- Coating film Heat compound Mobility bilityformability resistance Example 1 E-1 1.1 A A A Example 2 E-2 1 B A AExample 3 E-3 0.5 A A A Example 4 E-4 0.7 B A A Example 5 E-5 0.6 A A BExample 6 E-6 0.3 A A A Example 7 E-7 0.05 B A A Example 8 E-8 0.03 B AB Example 9 E-9 0.03 C A A Example 10 E-10 0.01 B A A Comparative C-1 NoC B N/A Example 1 Charac- teristics Comparative C-2 5 × 10⁻³ C B DExample 2

Examples 11 to 16, Comparative Examples 3 to 4

<Manufacturing of TFT Elements>

Respective evaluations were performed in the same manner as in Examples1 to 10 and Comparative Examples 1 to 2 except for mixing the specificcompound of the present invention or the comparative compound presentedin Table 61, the binder polymer presented in Table 61, and the solventpresented in Table 61 in the concentrations presented in Table 61,performing heating to 100° C., and using the resultant as thecomposition for forming the organic semiconductor film. The respectiveevaluation results are presented in Table 61.

Abbreviations used in Table 61 are as below.

-   -   PαMS: Poly(α-methylstyrene), Mw=300,000, manufactured by        Sigma-Aldrich Co. LLC.)    -   THF: Tetrahydrofuran

TABLE 61 Concentration Concentration of of binder semiconductor inpolymer in Coating Specific Binder composition composition Heat filmcompound polymer Solvent (mass %) (mass %) Mobility resistanceformability Example 11 E-1 PαMS Toluene 0.5 0.5 1.2 A A Example 12 E-2PαMS Toluene 0.5 0.5 1.2 A A Example 13 E-5 PαMS Toluene 0.5 0.5 0.8 A AExample 14 E-6 PαMS Toluene 0.5 0.5 0.5 A A Example 15 E-1 PαMS THF 0.50.5 0.1 B A Example 16 E-1 PαMS Toluene 0.5 12.0 0.02 B A ComparativeC-1 PαMS Toluene 0.5 0.5 2 × 10⁻³ D B Example 3 Comparative C-2 PαMSToluene 0.5 0.5 No N/A B Example 4 characteristics

Comparative Examples 5 to 21

The organic semiconductor films were formed in the same manner as inExample 1 to 16 except for weighing the specific compounds and toluene(1 mL) presented in Tables 60 and 61 and further the binder polymer (5mg) in the examples presented in Table 61 such that the content of therespective specific compounds become 21 mass %, performing mixture,performing heating to 100° C., and using the resultant as thecomposition for forming the organic semiconductor film. However, in allof Comparative Examples 5 to 21, due to insoluble matters, variousdefects were generated, and thus TFT characteristics were not exhibited.

EXPLANATION OF REFERENCES

-   -   10: substrate    -   20: gate electrode    -   30: gate insulating film    -   40: source electrode    -   42: drain electrode    -   50: organic semiconductor film    -   60: sealing layer    -   100,200: organic thin film transistor

What is claimed is:
 1. An organic semiconductor element comprising: acompound represented by Formula 1 below in an organic semiconductorlayer:

wherein, in Formula 1, X¹¹ and X¹² each independently represent achalcogen atom, Z^(1a) to Z^(1j) each independently represent a hydrogenatom or a halogen atom, A¹¹ represents ═CR^(A11)— or a nitrogen atom,R^(A11) represents a hydrogen atom or a group represented by R¹¹, A¹²represents ═CR^(A12)— or a nitrogen atom, R^(A12) represents a hydrogenatom or a group represented by R¹², n1 represents 0 or 1, p1 representsan integer of 0 to 2 in a case where A¹¹ is ═CR^(A11)— and represents 0or 1 in a case where A¹¹ is a nitrogen atom, q1 represents an integer of0 to 2 in a case where A¹² is ═CR^(A12)— and represents 0 or 1 in a casewhere A¹² is a nitrogen atom, at least one of p1 or q1 is not 0, R¹¹ andR¹² each independently represent a halogen atom, an aryl group, aheteroaryl group, or a group represented by Formula W below:—S^(W)-L^(W)-T^(W)  (W) wherein, in Formula W, S^(W) represents a singlebond or an alkylene group represented by —(CR^(S) ₂)_(k)—, R^(S) eachindependently represent a hydrogen atom or a halogen atom, k representsan integer of 1 to 17, L^(W) represents a single bond, a divalentlinking group represented by any one of Formulae L-1 to L-16 below, or agroup obtained by bonding any two or more of divalent linking groupsrepresented by Formulae L-1 to L-16 below, T^(W) represents an alkylgroup, a cyano group, a vinyl group, an ethynyl group, an aryl group, aheteroaryl group, an oxyethylene group, an oligooxyethylene group ofwhich the repetition number of oxyethylene units is two or greater, anoligosiloxane group having two or more silicon atoms, or a trialkylsilylgroup, and

wherein, in Formulae L-1 to L-16, * and wavy line portions representbonding positions to other structures, p13 represents an integer of 0 to4, p14, p15, and p16 each independently represent an integer of 0 to 2,R^(L1), R^(L21), R^(L22), R^(L13), R^(L14), R^(L15), and R^(L16) eachindependently represent a hydrogen atom or a substituent.
 2. The organicsemiconductor element according to claim 1, wherein all of Z^(1a) toZ^(1j) are hydrogen atoms.
 3. The organic semiconductor elementaccording to claim 1, wherein n1 is not
 0. 4. The organic semiconductorelement according to claim 1, wherein: at least one of R¹¹ or R¹² is agroup represented by Formula W.
 5. The organic semiconductor elementaccording to claim 1, wherein p1 and q1 are
 1. 6. The organicsemiconductor element according to claim 1, wherein both of X¹¹ and X¹²are S atoms, A¹¹ is ═CR^(A11)—, and A¹² is ═CR^(A12)—.
 7. The organicsemiconductor element according to claim 1, wherein a compoundrepresented by Formula 1 is a compound represented by Formula 2 below:

wherein, in Formula 2, X²¹ and X²² each independently represent achalcogen atom, W²¹ and W²² each independently represent a grouprepresented by Formula W.
 8. The organic semiconductor element accordingto claim 1, wherein the compound represented by Formula 1 is a linesymmetric structure.
 9. The organic semiconductor element according toclaim 1, wherein the number of carbon atoms in the group represented byFormula W is 5 to
 40. 10. The organic semiconductor element according toclaim 1, wherein L^(W) is a single bond, a divalent linking grouprepresented by any one of Formulae L-1 to L-4 and Formulae L-13 to L-16,or a divalent linking group obtained by bonding two or more divalentlinking groups represented by any one of Formulae L-1 to L-4 andFormulae L-13 to L-16.
 11. The organic semiconductor element accordingto claim 1, wherein L^(W) is a single bond or a divalent linking grouprepresented by any one of Formulae L-1 to L-4 and Formulae L-13 to L-16.12. The organic semiconductor element according to claim 1, whereinS^(W) is a single bond.
 13. The organic semiconductor element accordingto claim 1, wherein L^(W) is a single bond or a divalent linking grouprepresented by any one of Formula L-1 and Formulae L-13 to L-16.
 14. Theorganic semiconductor element according to claim 1, wherein T^(W) is analkyl group.
 15. The organic semiconductor element according to claim 1,wherein a group represented by Formula W is an alkyl group.
 16. Acomposition for forming an organic semiconductor film, comprising: asolvent having a boiling point of 100° C. or higher; and a compoundrepresented by Formula 1, wherein a content of the compound representedby Formula 1 is from 0.001% by mass to 15% by mass with respect to atotal amount of the composition for forming an organic semiconductorfilm:

wherein, in Formula 1, X¹¹ and X¹² each independently represent achalcogen atom, Z^(1a) to Z^(1j) each independently represent a hydrogenatom or a halogen atom, A¹¹ represents ═CR^(A11)— or a nitrogen atom,R^(A11) represents a hydrogen atom or a group represented by R¹¹, A¹²represents ═CR^(A12)— or a nitrogen atom, R^(A12) represents a hydrogenatom or a group represented by R¹², n1 represents 0 or 1, p1 representsan integer of 0 to 2 in a case where A¹¹ is ═CR^(A11)— and represents 0or 1 in a case where A¹¹ is a nitrogen atom, q1 represents an integer of0 to 2 in a case where A¹² is ═CR^(A12)—, and represents 0 or 1 in acase where A¹² is a nitrogen atom, R¹¹ and R¹² each independentlyrepresent a halogen atom, an aryl group, a heteroaryl group, or a grouprepresented by Formula W below:—S^(W)-L^(W)-T^(W)  (W) wherein, in Formula W, S^(W) represents a singlebond or an alkylene group represented by —(CR^(S) ₂)_(k)—, R^(S) eachindependently represent a hydrogen atom or a halogen atom, k representsan integer of 1 to 17, L^(W) represents a single bond, a divalentlinking group represented by any one of Formulae L-1 to L-16 below, or agroup obtained by bonding any two or more of divalent linking groupsrepresented by Formulae L-1 to L-16 below, T^(W) represents an alkylgroup, a cyano group, a vinyl group, an ethynyl group, an aryl group, aheteroaryl group, an oxyethylene group, an oligooxyethylene group ofwhich the repetition number of oxyethylene units is two or greater, anoligosiloxane group having two or more silicon atoms, or a trialkylsilylgroup, and

wherein, in Formulae L-1 to L-16, * and wavy line portions representbonding positions to other structures, p13 represents an integer of 0 to4, p14, p15, and p16 each independently represent an integer of 0 to 2,R^(L1), R^(L21), R^(L22), R^(L13), R^(L14), R^(L15), and R^(L16) eachindependently represent a hydrogen atom or a substituent.
 17. Thecomposition for forming an organic semiconductor film according to claim16, wherein all of Z^(1a) to Z^(1j) are hydrogen atoms.
 18. Thecomposition for forming an organic semiconductor film according to claim16, wherein n1 is
 0. 19. The composition for forming an organicsemiconductor film according to claim 16, wherein at least one of p1 orq1 is not
 0. 20. The composition for forming an organic semiconductorfilm according to claim 16, wherein: at least one of p1 or q1 is not 0,and at least one of R¹¹ or R¹² is a group represented by Formula W. 21.The composition for forming an organic semiconductor film according toclaim 16, wherein p1 and q1 is
 1. 22. The composition for forming anorganic semiconductor film according to claim 16, wherein both of X¹¹and X¹² are S atoms, A¹¹ is ═CR^(A11)—, and A¹² is ═CR^(A12)—.
 23. Thecomposition for forming an organic semiconductor film according to claim16, wherein the compound represented by Formula 1 is a compoundrepresented by Formula 2 below:

wherein, in Formula 2, X²¹ and X²² each independently represent achalcogen atom, W²¹ and W²² each independently represent a grouprepresented by Formula W.
 24. The composition for forming an organicsemiconductor film according to claim 16, wherein the compoundrepresented by Formula 1 is a line symmetric structure.
 25. Thecomposition for forming an organic semiconductor film according to claim16, wherein the number of carbon atoms in the group represented byFormula W is 5 to
 40. 26. The composition for forming an organicsemiconductor film according to claim 16, wherein L^(W) is a singlebond, a divalent linking group represented by any one of Formulae L-1 toL-4 and Formulae L-13 to L-16, and a divalent linking group obtained bybonding two or more divalent linking groups represented by any one ofFormulae L-1 to L-4 and Formulae L-13 to L-16.
 27. The composition forforming an organic semiconductor film according to claim 16, whereinL^(W) is a single bond or a divalent linking group represented by anyone of Formulae L-1 to L-4 and Formulae L-13 to L-16.
 28. Thecomposition for forming an organic semiconductor film according to claim16, wherein S^(W) is a single bond.
 29. The composition for forming anorganic semiconductor film according to claim 16, wherein L^(W) is asingle bond or a divalent linking group represented by any one ofFormula L-1 and Formulae L-13 to L-16.
 30. The composition for formingan organic semiconductor film according to claim 16, wherein T^(W) is analkyl group.
 31. The composition for forming an organic semiconductorfilm according to claim 16, wherein a group represented by Formula W isan alkyl group.
 32. The composition for forming an organic semiconductorfilm according to claim 16, further comprising: a binder polymer,wherein a content of the binder polymer is 10 mass % or less withrespect to a total amount of the composition for forming an organicsemiconductor film.
 33. A compound represented by Formula 1 below:

wherein, in Formula 1, X¹¹ and X¹² each independently represent achalcogen atom, Z^(1a) to Z^(1j) each independently represent a hydrogenatom or a halogen atom, A¹¹ represents ═CR^(A11)— or a nitrogen atom,R^(A11) represents a hydrogen atom or a group represented by R¹¹, A¹²represents ═CR^(A12)— or a nitrogen atom, R^(A12) represents a hydrogenatom or a group represented by R¹², n1 represents 0 or 1, p1 representsan integer of 0 to 2 in a case where A¹¹ is ═CR^(A11)— and represents 0or 1 in a case where A¹¹ is a nitrogen atom, q1 represents an integer of0 to 2 in a case where A¹² is ═CR^(A12)— and represents 0 or 1 in a casewhere A¹² is a nitrogen atom, at least one of p1 or q1 is not 0, R¹¹ andR¹² each independently represent a halogen atom, an aryl group, aheteroaryl group, or a group represented by Formula W below:—S^(W)-L^(W)-T^(W)  (W) wherein, in Formula W, S^(W) represents a singlebond or an alkylene group represented by —(CR^(S) ₂)_(k)—, R^(S) eachindependently represent a hydrogen atom or a halogen atom, k representsan integer of 1 to 17, L^(W) represents a single bond, a divalentlinking group represented by any one of Formulae L-1 to L-16 below, or agroup obtained by bonding any two or more of divalent linking groupsrepresented by Formulae L-1 to L-16 below, T^(W) represents an alkylgroup, a cyano group, a vinyl group, an ethynyl group, an aryl group, aheteroaryl group, an oxyethylene group, an oligooxyethylene group ofwhich the repetition number of oxyethylene units is two or greater, anoligosiloxane group having two or more silicon atoms, or a trialkylsilylgroup, and

wherein, in Formulae L-1 to L-16, * and wavy line portions representbonding positions to other structures, p13 represents an integer of 0 to4, p14, p15, and p16 each independently represent an integer of 0 to 2,R^(L1), R^(L21), R^(L22), R^(L13), R^(L14), R^(L15), and R^(L16) eachindependently represent a hydrogen atom or a substituent.
 34. A methodof manufacturing an organic semiconductor film, comprising: an applyingstep of applying the composition for forming an organic semiconductorfilm according to claim 16 to a substrate, and a removing step ofremoving at least a portion of the solvent having a boiling point of100° C. or higher included in the composition for forming an organicsemiconductor film.
 35. The method of manufacturing the organicsemiconductor film according to claim 34, wherein the applying step isperformed by an ink jet method or a flexographic printing method.
 36. Anorganic semiconductor film comprising the compound according to claim33.
 37. A method of manufacturing an organic semiconductor element,comprising: an applying step of applying the composition for forming anorganic semiconductor film according to claim 16 to a substrate, and aremoving step of removing at least a portion of the solvent having aboiling point of 100° C. or higher included in the composition forforming an organic semiconductor film.
 38. The method of manufacturingthe organic semiconductor element according to claim 37, wherein theapplying step is performed by an ink jet method or a flexographicprinting method.
 39. An organic semiconductor element comprising thecompound according to claim 33.